Compound for organic electric element, organic electric element using the same, and an electronic device thereof

ABSTRACT

Provided are a compound of Formula 2-K, an organic electric element including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, and an electronic device thereof, including the compound of Formula 2-K in the organic material layer, and thereby achieving lowered driving voltage, improved luminous efficiency, and extended life time.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a Divisional application of U.S. patent applicationSer. No. 17/309,771 filed on Jun. 17, 2021, which was a 371 ofPCT/KR2019/016359 filed on Nov. 26, 2019, which claims priority from andthe benefit under 35 U.S.C. § 119(a) of Korean Patent Application No.10-2018-0163432 filed on Dec. 17, 2018, the contents of which are herebyincorporated by reference for all purposes as if fully set forth herein.

BACKGROUND Technical Field

The present invention relates to compounds for organic electric element,organic electric element comprising the same, and electronic devicesthereof.

Background Art

In general, an organic light emitting phenomenon refers to a phenomenonin which electric energy is converted into light energy of an organicmaterial. An organic electric element utilizing the organic lightemitting phenomenon usually has a structure including an anode, acathode, and an organic material layer interposed therebetween. In manycases, the organic material layer has a multi-layered structure havingrespectively different materials in order to improve efficiency andstability of an organic electric element, and for example, may comprisea hole injection layer, a hole transport layer, a light emitting layer,an electron transport layer, an electron injection layer, or the like.

Materials used as an organic material layer in an organic electricelement may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, and the like according to its function. Further, thelight emitting material may be divided into a high molecular weight typeand a low molecular weight type according to its molecular weight, andmay also be divided into a fluorescent material derived from excitedsinglet states of electron and a phosphorescent material derived fromexcited triplet states of electron according to its light emittingmechanism. Further, the light emitting material may be divided intoblue, green, and red light emitting material and yellow and orange lightemitting material required for better natural color reproductionaccording to its light emitting color.

Meanwhile, when only one material is used as a light emitting material,there occur problems of shift of a maximum luminescence wavelength to alonger wavelength due to intermolecular interactions and lowering of theefficiency of a corresponding element due to deterioration in colorpurity or a reduction in luminous efficiency. On account of this, ahost/dopant system may be used as the light emitting material in orderto enhance the color purity and increase the luminous efficiency throughenergy transfer. This is based on the principle that if a small amountof dopant having a smaller energy band gap than a host forming a lightemitting layer is mixed in the light emitting layer, then excitonsgenerated in the light emitting layer are transported to the dopant,thus emitting light with high efficiency. With regard to this, since thewavelength of the host is shifted to the wavelength band of the dopant,light having a desired wavelength can be obtained according the type ofthe dopant.

Currently, the power consumption is required more than more as size ofdisplay becomes larger and larger in the portable display market.Therefore, the power consumption is very important factor in theportable display with a limited power source of the battery, andefficiency and life span issues must also be solved.

Efficiency, life span, driving voltage, and the like are correlated witheach other. If efficiency is increased, then driving voltage isrelatively lowered, and the crystallization of an organic material dueto Joule heating generated during operation is reduced as drivingvoltage is lowered. As a result, life span tends to increase. However,efficiency cannot be maximized only by simply improving the organicmaterial layer. This is because long life span and high efficiency canbe simultaneously achieved when an optimal combination of energy levelsand T₁ values, inherent material properties (mobility, interfacialproperties, etc.), and the like among the respective layers included inthe organic material layer is given.

Therefore, there is a need to develop a light emitting material that hashigh thermal stability and can efficiently a charge balance in thelight-emitting layer. That is, in order to allow an organic electricelement to fully exhibit excellent features, it should be prerequisiteto support a material constituting an organic material layer in theelement, for example, a hole injection material, a hole transportmaterial, a light emitting material, an electron transport material, anelectron injection material, or the like, by a stable and efficientmaterial. However, the stable and efficient material of organic materiallayer for an organic electric element has not been fully developed yet,in particular, it is strongly required to develop host material of thelight emitting layer.

Object, Technical Solution and Effects of the Invention

An object of the present invention is to provide compound lowering adriving voltage, improving luminous efficiency and lifetime of theelement, an organic electric element comprising the same, and anelectronic device thereof.

In an aspect of the present invention, the present invention provides anorganic electric element comprising the compound represented by Formula1 and the compound represented by Formula 2 and electronic devicesthereof.

In another aspect of the present invention, the present inventionprovides compound represented by the following Formula, an organicelectric element comprising the compound in a light emitting layer, andan electronic device thereof.

By using the compound according to embodiment of the present invention,a driving voltage of element can be lowered and the luminous efficiencyand lifetime of the element can be also remarkably improved.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates an example of an organic electroluminescent elementaccording to the present invention: 100 is an organic electric element,110 is a substrate, 120 is a first electrode, 130 is a hole injectionlayer, 140 is a hole transport layer, 141 is a buffer layer, 150 is alight emitting layer, 151 is an emission-auxiliary layer, 160 is anelectron transport layer, 170 is an electron injection layer, and 180 isa second electrode.

FIG. 2 illustrates Formula according to an aspect of the presentinvention.

DETAILED DESCRIPTION

Unless otherwise stated, the term “aryl group” or “arylene group” asused herein has, but not limited to, 6 to 60 carbon atoms. The arylgroup or arylene group in the present invention may comprise amonocyclic ring, ring assemblies, a fused polycyclic system,spiro-compounds and the like. In addition, unless otherwise stated, afluorenyl group may be comprised in an aryl group and a fluorenylenegroup may be comprised in an arylene group.

Unless otherwise stated, the term “fluorenyl group” or “fluorenylenegroup” as used herein means univalent or bivalent functional group inwhich R, R^(′)and R^(″)are all hydrogen in the following structure,“substituted fluorenyl group” or “substituted fluorenylene group” meansthat at least any one of R, R^(′) and R^(″) is a substituent other thanhydrogen, and the case where R and R^(′) are bonded to each other toform the spiro compound together with the carbon bonded to them iscomprised.

The term “spiro-compound” as used herein has a spiro union which meansunion having one atom as the only common member of two rings. The commonatom is designated as ‘spiro atom’. The compounds are defined as‘monospiro-’, ‘dispiro-’ or ‘trispiro-’ depending on the number of spiroatoms in one compound.

The term “heterocyclic group” used in the specification comprises anon-aromatic ring as well as an aromatic ring like “heteroaryl group” or“heteroarylene group”. Unless otherwise stated, the term “heterocyclicgroup” means, but not limited to, a ring containing one or moreheteroatoms and having 2 to 60 carbon atoms. Unless otherwise stated,the term “heteroatom” as used herein refers to N, O, S, P or Si andheterocyclic group means a monocyclic, ring assemblies, a fusedpolycyclic system or spiro compound containing a heteroatom.

The term “heterocyclic group” used in the specification may comprisecompound comprising a heteroatom group such as SO₂, P═O, etc., as thefollowing compounds, instead of carbon forming a ring.

The term “aliphatic ring group” as used herein refers to a cyclichydrocarbon except for aromatic hydrocarbons, and comprises a monocyclicring, ring assemblies, a fused polycyclic system, spiro compounds, andthe like, and unless otherwise specified, it means a ring of 3 to 60carbon atoms, but not limited thereto. For example, a fused ring formedby benzene being an aromatic ring with cyclohexane being a non-aromaticring corresponds to aliphatic ring group.

In this specification, a ‘group name’ corresponding to an aryl group, anarylene group, a heterocyclic group, and the like exemplified for eachsymbol and its substituent may be written in the name of functionalgroup reflecting the valence, and may also be described as the name of aparent compound. For example, in the case of phenanthrene which is akind of aryl group, it may be described by distinguishing valence suchas ‘phenanthryl (group)’ when it is ‘monovalent group’, and‘phenanthrylene (group)’ when it is ‘divalent group’, and regardless ofits valence, it may also be described as ‘phenanthrene’ which is aparent compound name. Similarly, in the case of pyrimidine, it may bedescribed as ‘pyrimidine’ regardless of its valence, and it may also bedescribed as the name of corresponding functional group such aspyrimidinyl (group) when it is ‘monovalent group’, and ‘pyrimidinylene(group)’ when it is ‘divalent group’.

In addition, in the present specification, the numbers and alphabetsindicating a position may be omitted when describing a compound name ora substituent name, For example, pyrido[4,3-d]pyrimidine,benzopuro[2,3-d] pyrimidine and 9,9-dimethyl-9H-fluorene can bedescribed as pyridopyrimidine, benzofurropyrimidine anddimethylfluorene, respectively. Therefore, both benzo[g]quinoxaline andbenzo[f] quinoxaline can be described as benzoquinoxaline.

In addition, unless otherwise expressed, where any formula of thepresent invention is represented by the following formula, thesubstituent according to the index may be defined as follows.

In the above formula, where a is an integer of zero, the substituent R¹is absent, that is, hydrogen atoms are bonded to all the carbonconstituting the benzene ring. Here, chemical formulas or compounds maybe written described by omitting the indication of hydrogen bonded tocarbon. In addition, one substituent R¹ is bonded to any carbon of thecarbons forming the benzene ring when “a” is an integer of 1. Similarly,where “a” is an integer of 2 or 3, for example, as in the followingformulas, substituents R¹s may be bonded to the carbon of the benzenering. Also, where “a” is an integer of 4 to 6, substituents R¹s arebonded to the carbon of the benzene ring in a similar manner. Further,where “a” is an integer of 2 or more, R¹s may be the same or differentfrom each other.

In addition, unless otherwise specified in the present specification,the ring formed by bonding between adjacent groups may be selected fromthe group consisting of a C₆-C₆₀ aromatic ring group, a fluorenyl group,a C₂-C₆₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P, a C₃-C₆₀ aliphaticring, a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromaticring group and a combination thereof.

Hereinafter, a laminated structure of the organic electric elementcomprising the compound of the present invention will be described withreference to FIG. 1.

In the following description of the present invention, a detaileddescription of known configurations and functions incorporated hereinwill be omitted when it may make the subject matter of the presentinvention rather unclear.

In addition, it will be understood that when an element such as a layer,film, region or substrate is referred to as being “on” or “over” anotherelement, it can be directly on the other element or intervening elementsmay also be present. In contrast, when an element is referred to asbeing “directly on” another element, there are no intervening elementspresent.

FIG. 1 illustrates an example of an organic electric element accordingto an embodiment of the present invention.

Referring to the FIG. 1, an organic electric element 100 according to anembodiment of the present invention includes a first electrode 120formed on a substrate 110, a second electrode 180, and an organicmaterial layer formed between the first electrode 120 and the secondelectrode 180 and comprising the compound of the present invention.Here, the first electrode 120 may be an anode (positive electrode), andthe second electrode 180 may be a cathode (negative electrode). In thecase of an inverted organic electroluminescent element, the firstelectrode may be a cathode, and the second electrode may be an anode.

The organic material layer may include a hole injection layer 130, ahole transport layer 140, a light emitting layer 150, an electrontransport layer 160, and an electron injection layer 170 stacked insequence on the first electrode 120. Here, at least one layer of theorganic material layer may be omitted, or a hole blocking layer, anelectron blocking layer, an emission-auxiliary layer 151, an electrontransport-auxiliary layer, a buffer layer 141, etc. may be furtherincluded in the organic material layer, and the electron transport layer160 or the like may serve as a hole blocking layer.

In addition, although not shown, the organic electric element accordingto an embodiment of the present invention may further include aprotective layer or a layer for improving luminous efficiency. The layerfor improving luminous efficiency may be formed on one side of sides ofthe first electrode or one side of sides of the second electrode,wherein the one side is not facing the organic material layer.

The inventive compound employed in the organic material layer may beused as a material of a hole injection layer 130, a hole transport layer140, an emission-auxiliary layer 151, an electron transport-auxiliarylayer, an electron transport layer 160 or an electron injection layer170, as host or dopant of a light emitting layer 150, or as a materialof a layer for improving luminous efficiency. Preferably, a mixture ofcompound of Formula 1 of the present invention and compound of Formula 2of the present invention can be used as host of a light emitting layer.Also, preferably, compound of Formula 2-K of the present invention canbe used as host of a light emitting layer.

On the other hand, even if the core is same or similar, the band gap,the electrical characteristics, the interface characteristics and thelike may be different depending on which substituent is bonded at whichposition. Therefore, there is a need to study the selection of the coreand the combination of the core and the sub-substituent bonded to thecore. In particular, long life span and high efficiency can besimultaneously achieved when the optimal combination of energy levelsand T₁ values, inherent material properties (mobility, interfacialproperties, etc.) and the like among the respective layers of an organicmaterial layer is achieved.

Therefore, the energy level and T₁ value between the respective layersof the organic material layer, inherent material properties (mobility,interfacial properties, etc.) and the like can be optimized by using amixture of compound of Formula 1 and compound of Formula 2 or compoundof Formula 2-K as host of a light emitting layer in the presentinvention.

The organic electric element according to an embodiment of the presentinvention may be manufactured using various deposition methods. Theorganic electric element according to an embodiment of the presentinvention may be manufactured using a PVD (physical vapor deposition)method or CVD (chemical vapor deposition) method. For example, theorganic electric element may be manufactured by depositing a metal, aconductive metal oxide, or alloy on the substrate to form the anode 120,forming the organic material layer including the hole injection layer130, the hole transport layer 140, the light emitting layer 150, theelectron transport layer 160, and the electron injection layer 170thereon, and then depositing a material which can be used as the cathode180, thereon. In addition, an emitting auxiliary layer 151 may be formedbetween a hole transport layer 140 and a light emitting layer 150, andan electron transport-auxiliary layer may be formed between a lightemitting layer 150 and an electron transport layer 160.

In addition, the organic material layer may be manufactured in such amanner that a smaller number of layers are formed using various polymermaterials by a soluble process or solvent process, for example, spincoating, nozzle printing, inkjet printing, slot coating, dip coating,roll-to-roll, doctor blading, screen printing, or thermal transfer,instead of deposition. Since the organic material layer according to thepresent invention may be formed in various ways, the scope of protectionof the present invention is not limited by a method of forming theorganic material layer.

The organic electric element according to an embodiment of the presentinvention may be of a top emission type, a bottom emission type, or adual emission type depending on the material used.

In addition, the organic electric element according to the presentinvention may be selected from group consisting of an organicelectroluminescent element, an organic solar cell, an organic photoconductor, an organic transistor, an element for monochromaticillumination and an element quantum dot display.

Another embodiment of the present invention provides an electronicdevice including a display device which includes the above describedorganic electric element, and a control unit for controlling the displaydevice. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electric dictionary, a point-to-multipoint (PMP), aremote controller, a navigation unit, a game player, various kinds ofTVs, various kinds of computers and so on.

Hereinafter, compound and an organic electric element according to anaspect of the present invention and will be described.

In one aspect of the present invention, the present invention providesan organic electric element comprising a first electrode, a secondelectrode, and an organic material layer formed between the firstelectrode and the second electrode, wherein the organic material layercomprises a phosphorescent light emitting layer, and host of thephosphorescent light emitting layer comprises a first compoundrepresented by Formula 1 and a second compound represented by Formula 2.

First, Formula 1 is described in detail.

In Formula 1, each of symbols is defined as follows:

X₁ is O or S.

Ar¹ and Ar² are each independently selected from the group consisting ofa C₆-C₁₈ aryl group, a fluorenyl group, a C₂-C₁₈ heterocyclic groupcomprising at least one heteroatom selected from the group consisting ofO, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, aC₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group anda C₆-C₃₀ aryloxy group.

Preferably, Ar¹ and Ar² are each independently selected from the groupconsisting of a C₆-C₁₈ aryl group, a fluorenyl group, a C₂-C₁₆heterocyclic group comprising at least one heteroatom selected from thegroup consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fusedring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀alkoxyl group and a C₆-C₃₀ aryloxy group.

Where Ar¹ and Ar² are each an aryl group, the aryl group may be phenyl,biphenyl, naphthyl, terphenyl, phenanthrene, pyrene, triphenylene,anthracene and the like. Where Ar¹ and Ar² are each a heterocyclicgroup, the heterocyclic group may be dibenzothiophene, dibenzofuran,carbazole, phenylcarbazole, benzonaphthofuran, benzonaphthothiophene andthe like. Where Ar¹ and Ar² are each a fluorenyl group, the fluorenylgroup may be 9,9-diphenylfluorene, 9,9-dimethylfluorene and the like.Where Ar¹ and Ar² are each aliphatic ring, the aliphatic ring may bepreferably a C₃-C₃₀ aliphatic ring, more preferably, a C₃-C₁₂ aliphaticring, for example, cyclohexane, cyclohexylcyclohexane, or the like.Where Ar¹ and Ar² are each an alkyl group, the alkyl group may bepreferably a C₂-C₁₀ alkyl group, for example, methyl, t-butyl and thelike. Where Ar¹ and Ar² are each an alkenyl group, the alkenyl group maybe preferably a C₂-C₁₀ alkenyl group, for example, ethene, propene andthe like.

L¹ to L³ are each independently selected from the group consisting of asingle bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀heterocyclic group comprising at least one heteroatom selected from thegroup consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and afused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

Where L¹ to L³ are each an arylene group, the arylene group may bepreferably a C₆-C₃₀ arylene group, more preferably a C₆-C₁₈ arylenegroup, for example, phenyl, biphenyl, naphthyl, terphenyl and the like.Where L¹ to L³ are each a heterocyclic group, the heterocyclic group maybe preferably a C₂-C₃₀ heterocyclic group, more preferably a C₂-C₁₈heterocyclic group, for example, carbazole, phenylcarbazole,dibenzofuran, dibenzothiophene and the like.

R¹ is selected from the group consisting of hydrogen, deuterium,halogen, a cyano group, a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀heterocyclic group comprising at least one heteroatom selected from thegroup consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fusedring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀alkoxyl group, a C₆-C₃₀ aryloxy group and -L′-N(R_(a))(R_(b)), andadjacent groups may be bonded to each other to form a ring.

a is an integer of 0-9, and where a is an integer of 2 or more, each ofa plurality of R¹s is the same as or different from each other.

The ring formed by bonding between neighboring R¹s may be a C₆-C₆₀aromatic ring group, a fluorenyl group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom of O, N, S, Si and P, a C₃-C₆₀aliphatic ring or a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀aromatic ring and the like. Where an aromatic ring is formed by bondingbetween neighboring R¹s, the aromatic ring may be preferably a C₆-C₃₀aromatic ring group, more preferably, a C₆-C₁₄ aromatic ring group, forexample, benzene, naphthalene, phenanthrene or the like.

Where R¹ is an aryl group, the aryl group may be preferably a C₆-C₃₀aryl group, more preferably a C₆-C₁₈ aryl group, for example, phenyl,naphthyl, biphenyl, terphenyl, phenanthrene, and the like.

L′ is selected from the group consisting of a single bond, a C₆-C₆₀arylene group, a fluorenylene group, a C₂-C₆₀ heterocyclic groupcomprising at least one heteroatom selected from the group consisting ofO, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and a fused ring of a C₃-C₆₀aliphatic ring with a C₆-C₆₀ aromatic ring.

R_(a) and R_(b) are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀heterocyclic group comprising at least one heteroatom selected from thegroup consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and afused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

Formula 1 may be represented by one of the following Formulas:

In Formulas 1-A to 1-G, each symbol can be defined as follows.

Ar¹, Ar², L¹-L³, X₁, R¹ and a are the same as defined for Formula 1.Preferably, in Formulas 1-F and 1-G, Ar¹ and Ar² are different from eachother, and preferably, Ar¹ and Ar² are each independently an aryl group,more preferably naphthyl.

X₂ and X₃ are each independently O or S.

R₄ and R₅ are each independently selected from the group consisting ofhydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising atleast one heteroatom selected from the group consisting of O, N, S, Siand P, a C₃-C₂₀ aliphatic ring, a fused ring of a C₃-C₂₀ aliphatic ringwith a C₆-C₂₀ aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenylgroup, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, a C₆-C₃₀ aryloxygroup and -L^(a)-N(R^(a))(R^(b)), and adjacent groups may be linked toeach other to form a ring.

‘The ring formed by bonding between neighboring groups’ may be a C₆-C₆₀aromatic ring group, a fluorenyl group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom of O, N, S, Si and P, a C₃-C₆₀aliphatic ring or a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀aromatic ring and the like. Where an aromatic ring is formed by bondingbetween neighboring R₄s or between neighboring R₅s, the aromatic ringmay be preferably a C₆-C₃₀ aromatic ring group, more preferably, aC₆-C₁₄ aromatic ring group, for example, benzene, naphthalene,phenanthrene or the like.

d′ is an integer of 0-7, e′ is an integer of 0-6, and where each ofthese is an integer of 2 or more, each of a plurality of R₄s, each of aplurality of R₅s are the same as or different from each other.

L^(a) is selected from the group consisting of a single bond, a C₆-C₂₀arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic groupcomprising at least one heteroatom selected from the group consisting ofO, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and a combination thereof.

R^(a) and R^(b) are each independently selected from the groupconsisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀heterocyclic group comprising at least one heteroatom selected from thegroup consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and acombination thereof.

Preferably, each symbol in the above Formulas may be furthersubstituted. For example, in Formula 1, Formulas 1-A to 1-G, Ar¹, Ar²,L¹-L³, L′, L^(a), R¹, R₄, R₅, R_(a), R_(b), R^(a), R^(b), and the ringformed by bonding between adjacent groups may be each optionallysubstituted with one or more substituents selected from the groupconsisting of deuterium, halogen, a silane group unsubstituted orsubstituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxanegroup, a boron group, a germanium group, a cyano group, a nitro group, aC₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, aC₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, afluorenyl group, a C₂-C₂₀ heterocyclic group containing at least oneheteroatom of O, N, S, Si, and P, a C₃-C₂₀ aliphatic ring group, aC₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group.

Specifically, the compound represented by Formula 1 may be one of thefollowing compounds, but it is not limited only thereto:

Next, Formula 2 is described in detail.

In Formula 2, each of symbols may be defined as follows:

W¹ and W² are each independently a single bond, N-L′-(Ar⁴), O, S orC(R^(′))(R^(″)), with the proviso that the case where both W¹ and W² area single bond is excluded.

Ar³ and Ar⁴ are each independently selected from the group consisting ofa C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic groupcomprising at least one heteroatom selected from the group consisting ofO, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, aC₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group anda C₆-C₃₀ aryloxy group.

Where Ar³ and Ar⁴ are each an aryl group, the aryl group may bepreferably a C₆-C₃₀ aryl group, more preferably a C₆-C₁₈ aryl group, forexample, phenyl, biphenyl, naphthyl, phenanthrene, terphenyl, phenalene,triphenylene and the like.

Where Ar³ and Ar⁴ are each a heterocyclic group, the heterocyclic groupmay be preferably a C₂-C₃₀ heterocyclic group, more preferably a C₂-C₁₆heterocyclic group, for example, pyridine, pyrimidine, triazine,quinazoline, benzoquinazoline, dibenzoquinazoline, quinoxaline,benzothienopyrimidine, benzofuropyrimidine, thienopyrimidine,furopyrimidine, naphthofuropyrimidine, naphthofuropyrazine,benzothiophene, dibenzothiophene, benzonaphthothiophene, benzofuran,dibenzofuran, benzonaphthofuran and the like.

Where Ar³ and Ar⁴ are each a fluorenyl group, the fluorenyl group may be9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9′-spirobifluoreneand the like.

R² to R⁴ are each independently selected from the group consisting ofhydrogen, deuterium, halogen, a cyano group, a C₆-C₆₀ aryl group, afluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least oneheteroatom selected from the group consisting of O, N, S, Si and P, aC₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀ aliphatic ring with aC₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, aC₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxy group and-L′-N(R_(a))(R_(b)), and adjacent R²s, adjacent R³s or adjacent R⁴s maybe bonded to each other to form a ring.

The ring formed by bonding between neighboring groups may be a C₆-C₆₀aromatic ring group, a fluorenyl group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom of O, N, S, Si and P, a C₃-C₆₀aliphatic ring or a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀aromatic ring and the like. Where an aromatic ring is formed by bondingbetween neighboring groups, the aromatic ring may be preferably a C₆-C₃₀aromatic ring group, more preferably, a C₆-C₁₄ aromatic ring group, forexample, benzene, naphthalene, phenanthrene or the like.

b and d are each an integer of 0-4, c is an integer of 0-2, and whereeach of these is an integer of 2 or more, each of a plurality of R²s,each of a plurality of R³s and each of a plurality of R⁴s are the sameas or different from each other.

Where R² to R⁴ are each an aryl group, the aryl group may be preferablya C₆-C₃₀ aryl group, more preferably a C₆-C₁₈ aryl group, for example,phenyl, biphenyl, naphthyl, terphenyl and the like.

Where R² to R⁴ are each an alkoxy group, the alkoxy group may bepreferably a C₁-C₁₀ alkoxy group, for example, a methoxy group, anethoxy group, or the like.

R^(′) and R^(″) are each independently selected from the groupconsisting of hydrogen, deuterium, halogen, a cyano group, a C₆-C₆₀ arylgroup, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising atleast one heteroatom selected from the group consisting of O, N, S, Siand P, a C₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀ aliphatic ringwith a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenylgroup, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxygroup and -L^(′)-N(R_(a))(R_(b)), and R^(′) and R^(″) may be bonded toeach other to form a ring. When R^(′) and R^(″) combine with each otherto form a ring, a spiro compound may be formed.

Where R^(′) and R^(″) are each an alkyl group, the alkyl group may bepreferably a C₁-C₂₀ alkyl group, more preferably a C₁-C₁₀ alkyl group,for example, methyl, ethyl, or the like.

When R^(′) and R^(″) are each aryl group, the aryl group may bepreferably C₆-C₃₀ aryl groups, more preferably C₆-C₁₈ aryl group, forexample, phenyl, biphenyl, naphthyl, terphenyl, or the like.

L⁴ and L′ are each independently selected from the group consisting of asingle bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀heterocyclic group comprising at least one heteroatom selected from thegroup consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and afused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

Where L⁴ and L′ are each an arylene group, the arylene group may bepreferably a C₆-C₃₀ arylene group, more preferably a C₆-C₁₈ arylenegroup, for example, phenyl, biphenyl, naphthyl, terphenyl, phenanthreneand the like.

Where L⁴ and L′ are each a heterocyclic group, the heterocyclic groupmay be preferably a C₂-C₃₀ heterocyclic group, more preferably a C₂-C₁₆heterocyclic group, for example, pyridine, pyrimidine, triazine,quinazoline, benzoquinazoline, quinoxaline, furopyrimidine,thienopyrimidine, benzothienopyrimidine, benzofuropyrimidine,naphthofuropyrimidine, naphthothienopyrimidine, naphthofuropyrazine,benzothiophene, dibenzothiophene, benzofuran, dibenzofuran, and thelike.

R_(a) and R_(b) are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀heterocyclic group comprising at least one heteroatom selected from thegroup consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and afused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

R² to R⁴, Ar³, Ar⁴, L⁴, L^(′), R_(a), R_(b), R^(′), R^(″), and the ringformed by bonding between adjacent groups may be each optionallysubstituted with one or more substituents selected from the groupconsisting of deuterium, halogen, a silane group unsubstituted orsubstituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxanegroup, a boron group, a germanium group, a cyano group, a nitro group, aC₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, aC₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, afluorenyl group, a C₂-C₂₀ heterocyclic group containing at least oneheteroatom of O, N, S, Si, and P, a C₃-C₂₀ aliphatic ring group, aC₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group.

Formula 2 may be represented by one of Formulas 2-A to 2-I:

In Formulas 2-A to 2-I, Ar³, L⁴, R²-R⁴, W¹, W² and b to d are the sameas defined for Formula 2.

In addition, Formula 2 may be represented by Formula 2-J:

In Formula 2-J, each symbol can be defined as follows:

L⁴, R²-R⁴, W¹, W², b to d are the same as defined for Formula 2, and W³is O or S.

R¹¹ may be defined the same as R². In other words, R¹¹ is selected fromthe group consisting of hydrogen, deuterium, halogen, a cyano group, aC₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic groupcomprising at least one heteroatom selected from the group consisting ofO, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, aC₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group, aC₆-C₃₀ aryloxy group and -L′-N(R_(a))(R_(b)), and adjacent R¹¹s may bebonded to each other to form a ring.

The ring formed by bonding between neighboring R¹¹s may be a C₆-C₆₀aromatic ring group, a fluorenyl group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom of O, N, S, Si and P, a C₃-C₆₀aliphatic ring or a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀aromatic ring and the like. Where an aromatic ring is formed by bondingbetween neighboring R¹¹s, the aromatic ring may be preferably a C₆-C₃₀aromatic ring group, more preferably, a C₆-C₁₄ aromatic ring group, forexample, benzene, naphthalene, phenanthrene or the like.

d1 is an integer of 0-9, and where d1 is an integer of 2 or more, eachof a plurality of R¹¹s are the same as or different from each other.

Specifically, the compound represented by Formula 2 may be one of thefollowing compounds, but it is not limited only thereto:

Preferably, in Formulas 1 and 2, L¹ to L⁴ may be each independently oneof the following Formulas b-1 to b-13:

In Formulas b-1 to b-13, each of symbols may be defined as follows:

R⁵ to R⁷ are each independently selected from the group consisting ofhydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising atleast one heteroatom selected from the group consisting of O, N, S, Siand P, a C₃-C₂₀ aliphatic ring, a fused ring of a C₃-C₂₀ aliphatic ringwith a C₆-C₂₀ aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenylgroup, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, a C₆-C₃₀ aryloxygroup and -L^(a)-N(R^(a))(R^(b)), and adjacent groups may be bonded toeach other to form a ring.

‘The ring formed by bonding between neighboring groups’ may be a C₆-C₆₀aromatic ring group, a fluorenyl group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom of O, N, S, Si and P, a C₃-C₆₀aliphatic ring or a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀aromatic ring and the like. Where an aromatic ring is formed by bondingbetween neighboring R⁴s, or neighboring R⁵s, the aromatic ring may bepreferably a C₆-C₃₀ aromatic ring group, more preferably, a C₆-C₁₄aromatic ring group, for example, benzene, naphthalene, phenanthrene orthe like.

Y is N-(L^(a)-Ar^(a)), O, S or C(R^(′))(R^(″)).

Z¹ to Z³ are each independently C, C(R^(′)) or N, and at least one of Z¹to Z³ is N.

f is an integer of 0-6, e, g, h and i are each an integer of 0-4, j andk are each an integer of 0-3, l is an integer of 0-2, m is an integer of0-3, and where each of these is an integer of 2 or more, each of aplurality of R⁵, each of a plurality of R⁶, and each of a plurality ofR⁷ are the same as or different from each other.

R^(′) and R^(″) are each independently selected from the groupconsisting of hydrogen, deuterium, halogen, a cyano group, a nitrogroup, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclicgroup comprising at least one heteroatom selected from the groupconsisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a fused ringof a C₃-C₂₀ aliphatic ring with a C₆-C₂₀ aromatic ring, a C₁-C₂₀ alkylgroup, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxylgroup, a C₆-C₃₀ aryloxy group, and -L^(a)-N(R^(a))(R^(b)).

R^(′) and R^(″) in C(R^(′))(R^(″)) may be linked to each other to form aring, and adjacent R^(′)s in C(R^(′)) may be linked to each other toform a ring.

Ar^(a) is selected from the group consisting of a C₆-C₂₀ aryl group, afluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least oneheteroatom selected from the group consisting of O, N, S, Si and P, aC₃-C₂₀ aliphatic ring, and a combination thereof.

L^(a) is selected from the group consisting of a single bond, a C₆-C₂₀arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic groupcomprising at least one heteroatom selected from the group consisting ofO, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and a combination thereof.

R^(a) and R^(b) are each independently selected from the groupconsisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀heterocyclic group comprising at least one heteroatom selected from thegroup consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and acombination thereof.

R⁵ to R⁷, L^(a), Ar^(a), R^(′), R^(″), R^(a), R^(b) and the ring formedby bonding between adjacent groups may be each optionally substitutedwith one or more substituents selected from the group consisting ofdeuterium, halogen, a silane group unsubstituted or substituted with aC₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxane group, a borongroup, a germanium group, a cyano group, a nitro group, a C₁-C₂₀alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₁-C₂₀alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀aryl group, a C₆-C₂₀ aryl group substituted with deuterium, a fluorenylgroup, a C₂-C₂₀ heterocyclic group containing at least one heteroatom ofO, N, S, Si, and P, a C₃-C₂₀ aliphatic ring group, a C₇-C₂₀ arylalkylgroup and C₈-C₂₀ arylalkenyl group.

In another aspect of the present invention, the present inventionprovides a compound represented by Formula 2-K:

In Formula 2-K, R²-R⁴, R¹¹, W¹, W², W³, b-d and d1 are the same asdefined for Formula 2-J, L⁴ is a single bond or a C₆-C₁₂ arylene group.

Preferably, Formula 2-K may be represented by Formula 2-K-1 or Formula2-K-2:

In Formulas above, W¹-W³, R²-R⁴, R¹¹, L⁴, b-d and d1 are the same asdefined for Formula 2-K.

R² to R⁴, R¹¹ and L⁴ may be each further substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, asilane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or aC₆-C₂₀ aryl group, a siloxane group, a boron group, a germanium group, acyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxygroup, a C₆-C₂₀ aryloxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenylgroup, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl groupsubstituted with deuterium a fluorenyl group, a C₂-C₂₀ heterocyclicgroup containing at least one heteroatom of O, N, S, Si, and P, a C₃-C₂₀aliphatic ring group, a C₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenylgroup.

Specifically, the compound represented by Formula 2-K may be one of thefollowing compounds, but it is not limited only thereto:

In another aspect, the present invention provides an organic electricelement comprising a first electrode, a second electrode, and an organicmaterial layer formed between the first electrode and the secondelectrode, wherein the organic material layer comprises compoundrepresented by Formula 2-K. Preferably, the organic material layercomprises a light emitting layer which comprises a compound representedby Formula 2-K.

Hereinafter, examples for synthesizing the compounds represented byFormulas 1 and 2 according to the present invention and examples forpreparing an organic electric element according to the present inventionwill be described in detail with reference to examples, but the presentinvention is not limited to the following examples.

[Synthesis Example 1] Formula 1

The compound represented by Formula 1 according to the present inventioncan be synthesized by reacting Sub 1 and Sub 2 as shown in ReactionScheme 1, but there is no limitation thereto.

1. Exemplary Compounds and Synthesis Examples of Sub 1

Compounds belong to Sub 1 of Reaction Scheme 1 are as follows, but thereis no limitation thereto.

FD-MS (Field Desorption-Mass Spectrometry) values of compounds belong toSub 1 are shown in Table 1 below.

TABLE 1 Compound FD-MS Compound FD-MS Sub 1-1 m/z = 344.16(C₂₂H₂₁BO₃ =344.22) Sub 1-2 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub 1-3 m/z =344.16(C₂₂H₂₁BO₃ = 344.22) Sub 1-4 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub1-5 m/z = 470.21(C₃₂H₂₇BO₃ = 470.38) Sub 1-6 m/z = 344.16(C₂₂H₂₁BO₃ =344.22) Sub 1-7 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub 1-8 m/z =344.16(C₂₂H₂₁BO₃ = 344.22) Sub 1-9 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub1-10 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub 1-11 m/z = 344.16(C₂₂H₂₁BO₃ =344.22) Sub 1-12 m/z = 520.22(C₃₆H₂₉BO₃ = 520.44) Sub 1-13 m/z =420.19(C₂₈H₂₆BO₃ = 420.32) Sub 1-14 m/z = 436.17(C₂₈H₂₅BO₂S = 436.38)Sub 1-15 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28) Sub 1-16 m/z =360.14(C₂₂H₂₁BO₂S = 360.28) Sub 1-17 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28)Sub 1-18 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28) Sub 1-28 m/z =496.22(C₃₄H₂₉BO₃ = 496.41) Sub 1-30 m/z = 420.19(C₂₈H₂₅BO₃ = 420.32) Sub1-36 m/z = 470.21(C₃₂H₂₇BO₃ = 470.38) Sub 1-66 m/z = 510.2(C₃₄H₂₇BO₄ =510.4) Sub 1-68 m/z = 526.18(C₃₄H₂₇BO₃S = 526.46) Sub 1-69 m/z =560.22(C₃₈H₂₉BO₄ = 560.46) Sub 1-70 m/z = 576.19(C₃₈H₂₉BO₃S = 576.52)Sub 1-90 m/z = 496.22(C₃₄H₂₉BO₃ = 496.41) Sub 1-92 m/z =546.24(C₃₈H₃₁BO₃ = 546.47) Sub 1-93 m/z = 470.21(C₃₂H₂₇BO₃ = 470.38) Sub1-94 m/z = 436.17(C₂₈H₂₅BO₂S = 436.38) Sub 1-97 m/z = 486.18(C₃₂H₂₇BO₂S= 486.44) Sub 1-105 m/z = 592.17(C₃₈H₂₉BO₂S₂ = 592.58) Sub 1-106 m/z =526.18(C₃₄H₂₇BO₃S = 526.46) Sub 1-107 m/z = 576.19(C₃₈H₂₉BO₃S = 576.52)Sub 1-108 m/z = 542.15(C₃₄H₂₇BO₂S₂ = 542.52) Sub 1-118 m/z =586.23(C₄₀H₃₁BO₄ = 586.49) Sub 1-119 m/z = 652.22(C₄₄H₃₃BO₃S = 652.62)Sub 1-120 m/z = 618.19(C₄₀H₃₁BO₂S₂ = 618.62) Sub 1-121 m/z =602.21(C₄₀H₃₁BO₃S = 602.56)

Sub 1 of Reaction Scheme 1 may be synthesized by the reaction route ofthe following Reaction Scheme 2, but are not limited thereto.

Synthesis Example of Sub 1-3

After adding bis(pinacolato)diboran (CAS Registry Number: 73183-34-3)(33.28 g, 131.04 mmol), PdCl₂(dppf) (2.92 g, 3.57 mmol), KOAc (35.07 g,357.40 mmol) and DMF (596 ml) to 2-bromonaphtho[2,3-b]benzofuran (35.4g, 119.13 mmol), the mixture was stirred under reflux. When the reactionwas completed, the reaction product was extracted with ether and water.An organic layer was concentrated and the concentrate was dried overMgSO₄ and concentrated. Then, the concentrate was separated by a silicagel column and recrystallized to obtain 34.86 g (yield: 85%) of theproduct.

Synthesis Example of Sub 1-21

Bis(pinacolato)diboran (CAS Registry Number: 73183-34-3) (31.57 g,124.33 mmol), PdCl₂(dppf) (2.77 g, 3.39 mmol), KOAc (33.28 g, 339.07mmol) and DMF (565 ml) were added to8-bromobenzo[b]naphtho[2,3-d]thiophene (35.40 g, 113.02 mmol), and thereaction was carried out in the same manner as in the synthesis methodof 1-3 to obtain 33.39 g (yield: 82%) of the product.

Synthesis Example of Sub 1-37

(1) Synthesis of Sub 1-37a

After adding 1-bromo-4-iodonaphthalene (69.65 g, 209.17 mmol), Pd(PPh₃)₄(8.06 g, 6.97 mmol), K₂CO₃ (72.27 g, 522.92 mmol), THF (639 ml) andwater (320 ml) to4,4,5,5-tetramethyl-2-(naphtho[2,3-b]benzofuran-2-yl)-1,3,2-dioxaborolane(60 g, 174.31 mmol), the mixture was stirred under reflux. When thereaction was completed, the reaction product was extracted with etherand water. An organic layer was concentrated and the concentrate wasdried over MgSO₄ and concentrated. Then, the concentrate was separatedby a silica gel column and recrystallized to obtain 45.01 g (yield: 61%)of the product.

(2) Synthesis of Sub 1-37

Bis(pinacolato)diboran (CAS Registry Number: 73183-34-3) (29.70 g,116.96 mmol), PdCl₂(dppf) (2.60 g, 3.19 mmol), KOAc (31.31 g, 318.99mmol) and DMF (532 ml) were added to Sub 1-37a (45.01 g, 106.33 mmol),and the reaction was carried out in the same manner as in the synthesismethod of 1-3 to obtain 39.01 g (yield: 78%) of the product.

Synthesis Example of Sub 1-68

(1) Synthesis of Sub 1-68a

1-bromo-8-iododibenzo[b,d]thiophene (81.38 g, 209.17 mmol), Pd(PPh₃)₄(8.06 g, 6.97 mmol), K₂CO₃ (72.27 g, 522.92 mmol), THF (639 ml) andwater (320 ml) were added to4,4,5,5-tetramethyl-2-(naphtho[2,3-b]benzofuran-2-yl)-1,3,2-dioxaborolane(60 g, 174.31 mmol), and the reaction was carried out in the same manneras in the synthesis method of Sub 1-37a to obtain 56.82 g (yield: 68%)of the product.

(2) Synthesis of Sub 1-68

Bis(pinacolato)diboran (CAS Registry Number: 73183-34-3) (33.11 g,130.38 mmol), PdCl₂(dppf) (2.90 g, 3.56 mmol), KOAc (34.90 g, 355.58mmol) and DMF (593 ml) were added to Sub 1-68a (56.82 g, 118.53 mmol),and the reaction was carried out in the same manner as in the synthesismethod of 1-3 to obtain 46.80 g (yield: 75%) of the product.

Synthesis Example of Sub 1-98

(1) Synthesis of Sub 1-98a

1-bromo-5-iodonaphthalene (66.54 g, 199.84 mmol), Pd(PPh₃)₄ (7.70 g,6.66 mmol), K₂CO₃ (69.05 g, 499.61 mmol), THF (611 ml) and water (305ml) were added to2-(benzo[b]naphtho[2,3-d]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(60 g, 166.54 mmol), and the reaction was carried out in the same manneras in the synthesis method of Sub 1-37a to obtain 46.83 g (yield: 64%)of the product.

(2) Synthesis of Sub 1-98

Bis(pinacolato)diboran (CAS Registry Number: 73183-34-3) (29.77 g,117.24 mmol), PdCl₂(dppf) (2.61 g, 3.20 mmol), KOAc (31.38 g, 319.75mmol) and DMF (533 ml) were added to 1-98a (46.83 g, 106.58 mmol), andthe reaction was carried out in the same manner as in the synthesismethod of 1-3 to obtain 37.33 g (yield: 72%) of the product.

6. Synthesis Example of Sub 1-111

(1) Synthesis of Sub 1-111a

1-bromo-8-iododibenzo[b,d]thiophene (77.75 g, 199.84 mmol), Pd(PPh₃)₄(7.70 g, 6.66 mmol), K₂CO₃ (69.05 g, 499.61 mmol), THF (611 ml) andwater (305 ml) were added to2-(benzo[b]naphtho[2,3-d]thiophen-11-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(60 g, 166.54 mmol), and the reaction was carried out in the same manneras in the synthesis method of Sub 1-37a to obtain 54.46 g (yield: 66%)of the product.

(2) Synthesis of Sub 1-111

Bis(pinacolato)diboran (CAS Registry Number: 73183-34-3) (30.70 g,120.91 mmol), PdCl₂(dppf) (2.69 g, 3.30 mmol), KOAc (32.36 g, 329.76mmol) and DMF (550 ml) were added to Sub 1-111a (54.46 g, 109.92 mmol),and the reaction was carried out in the same manner as in the synthesismethod of 1-3 to obtain 41.15 g (yield: 69%) of the product.

2. Exemplary Compounds and Synthesis Examples of Sub 2

Compounds belong to Sub 2 of Reaction Scheme 1 are as follows, but arenot limited thereto.

FD-MS values of compounds belong to Sub 2 are shown in Table 2 below.

TABLE 2 Compound FD-MS Compound FD-MS Sub 2-1 m/z = 267.06(C₁₅H₁₀ClN₃ =267.72) Sub 2-2 m/z = 343.09(C₂₁H₁₄ClN₃ = 343.81) Sub 2-4 m/z =317.07(C₁₉H₁₂ClN₃ = 317.78) Sub 2-5 m/z = 495.15(C₃₃H₂₂ClN₃ = 496.01)Sub 2-7 m/z = 367.09(C₂₃H₁₄ClN₃ = 367.84) Sub 2-8 m/z =493.13(C₃₃H₂₀ClN₃ = 493.99) Sub 2-9 m/z = 393.1(C₂₅H₁₆ClN₃ = 393.87) Sub2-10 m/z = 519.15(C₃₅H₂₂ClN₃ = 520.03) Sub 2-11 m/z = 469.13(C₃₁H₂₀ClN₃= 469.97) Sub 2-12 m/z = 393.1(C₂₅H₁₆ClN₃ = 393.87) Sub 2-14 m/z =367.09(C₂₃H₁₄ClN₃ = 367.84) Sub 2-19 m/z = 423.06(C₂₅H₁₄ClN₃S = 423.92)Sub 2-20 m/z = 449.08(C₂₇H₁₆ClN₃S = 449.96) Sub 2-21 m/z =373.04(C₂₁H₁₂ClN₃S = 373.86) Sub 2-22 m/z = 433.1(C₂₇H₁₆ClN₃O = 433.9)Sub 2-24 m/z = 357.07(C₂₁H₁₂ClN₃O = 357.8) Sub 2-25 m/z =525.11(C₃₃H₂₀ClN₃S = 526.05) Sub 2-27 m/z = 473.13(C₃₀H₂₀ClN₃O = 473.96)Sub 2-28 m/z = 473.08(C₂₉H₁₆ClN₃S = 473.98) Sub 2-31 m/z =538.1(C₃₃H₁₉ClN₄S = 539.05) Sub 2-32 m/z = 523.11(C₃₃H₁₈ClN₃O₂ = 523.98)Sub 2-33 m/z = 509.13(C₃₃H₂₀ClN₃O = 509.99) Sub 2-34 m/z =575.12(C₃₇H₂₂ClN₃S = 576.11) Sub 2-37 m/z = 584.18(C₃₉H₂₅ClN₄ = 585.11)Sub 2-39 m/z = 483.11(C₃₁H₁₈ClN₃O = 483.96) Sub 2-40 m/z =509.13(C₃₃H₂₀ClN₃O = 509.99) Sub 2-42 m/z = 499.09(C₃₁H₁₈ClN₃S = 500.02)Sub 2-43 m/z = 575.12(C₃₇H₂₂ClN₃S = 576.11) Sub 2-44 m/z =533.13(C₃₅H₂₀ClN₃O = 534.02) Sub 2-45 m/z = 407.08(C₂₅H₁₄ClN₃O = 407.86)Sub 2-47 m/z = 423.06(C₂₅H₁₄ClN₃S = 423.92) Sub 2-50 m/z =449.08(C₂₇H₁₆ClN₃S = 449.96) Sub 2-51 m/z = 433.1(C₂₇H₁₆ClN₃O = 433.9)Sub 2-52 m/z = 419.12(C₂₇H₁₈ClN₃ = 419.91) Sub 2-54 m/z =383.12(C₂₄H₁₈ClN₃ = 383.88) Sub 2-55 m/z = 357.07(C₂₁H₁₂ClN₃O = 357.8)Sub 2-56 m/z = 539.09(C₃₃H₁₈ClN₃OS = 540.04) Sub 2-57 m/z =320.08(C₁₈H₁₃ClN₄ = 320.78) Sub 2-58 m/z = 363.11(C₂₁H₁₈ClN₃O = 363.85)Sub 2-59 m/z = 432.11(C₂₇H₁₇ClN₄ = 432.91) Sub 2-60 m/z =508.15(C₃₃H₂₁ClN₄ = 509.01) Sub 2-64 m/z = 433.1(C₂₇H₁₆ClN₃O = 433.9)Sub 2-66 m/z = 559.15(C₃₇H₂₂ClN₃O = 560.05) Sub 2-67 m/z =483.11(C₃₁H₁₃ClN₃O = 483.96) Sub 2-69 m/z = 573.11(C₃₇H₂₀ClN₃S = 574.1)Sub 2-80 m/z = 495.15(C₃₃H₂₂ClN₃ = 496.01) Sub 2-84 m/z =634.19(C₄₃H₂₇ClN₄ = 635.17) Sub 2-94 m/z = 347.08(C₂₀H₁₄ClN₃O = 347.8)Sub 2-95 m/z = 324.12(C₁₉H₅D₇ClN₃ = 324.82) Sub 2-96 m/z =499.07(C₂₉H₁₄ClN₅S = 499.98) Sub 2-97 m/z = 433.04(C₂₁H₉ClF₅N₃ = 433.77)Sub 2-98 m/z = 398.13(C₂₅H₁₁D₅ClN₃ = 398.9) Sub 2-99 m/z =459.11(C₂₉H₁₈ClN₃O = 459.93) Sub 2-100 m/z = 447.11(C₂₈H₁₈ClN₃O =447.92) Sub 2-101 m/z = 433.13(C₂₈H₂₀ClN₃ = 433.94) Sub 2-102 m/z =469.13(C₃₁H₂₀ClN₃ = 469.97) Sub 2-103 m/z = 559.15(C₃₇H₂₂ClN₃O = 560.05)

Sub 2 of Reaction Scheme 1 may be synthesized by the reaction route ofthe following Reaction Scheme 3, but are not limited thereto.

Synthesis Example of Sub 2-2

After adding [1,1′-biphenyl]-3-ylboronic acid (31.01 g, 156.60 mmol),Pd(PPh₃)₄ (7.24 g, 6.26 mmol), K₂CO₃ (64.93 g, 469.79 mmol), THF (522ml) and water (261 ml) to 2,4-dichloro-6-phenyl-1,3,5-triazine (35.4 g,156.60 mmol), the mixture was stirred under reflux. When the reactionwas completed, the reaction product was extracted with ether and water.An organic layer was concentrated and the concentrate was dried overMgSO₄ and concentrated. Then, the concentrate was separated by a silicagel column and recrystallized to obtain 43.07 g (yield: 80%) of theproduct.

Synthesis Example of Sub 2-6

Naphthalen-1-ylboronic acid (26.93 g, 156.60 mmol), Pd(PPh₃)₄ (7.24 g,6.26 mmol), K₂CO₃ (64.93 g, 469.79 mmol), THF (522 ml) and water (261ml) were added to 2,4-dichloro-6-phenyl-1,3,5-triazine (35.4 g, 156.60mmol), and the reaction was carried out in the same manner as in thesynthesis method of Sub 2-2 to obtain 36.82 g (yield: 74%) of theproduct.

Synthesis Example of Sub 2-22

Dibenzo[b,d]thiophen-4-ylboronic acid (26.72 g, 117.16 mmol), Pd(PPh₃)₄(5.42 g, 4.69 mmol), K₂CO₃ (48.58 g, 351.47 mmol), THF (391 ml) andwater (195 ml) were added to2-([1,1′-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine (35.4 g, 117.16mmol), and the reaction was carried out in the same manner as in thesynthesis method of Sub 2-2 to obtain 40.06 g (yield: 76%) of theproduct.

Synthesis Example of Sub 2-24

Dibenzo[b,d]furan-1-ylboronic acid (33.20 g, 156.60 mmol), Pd(PPh₃)₄(7.24 g, 6.26 mmol), K₂CO₃ (64.93 g, 469.79 mmol), THF (522 ml) andwater (261 ml) were added to 2,4-dichloro-6-phenyl-1,3,5-triazine (35.4g, 156.60 mmol), and the reaction was carried out in the same manner asin the synthesis method of Sub 2-2 to obtain 38.66 g (yield: 69%) of theproduct.

Synthesis Example of Sub 2-47

Benzo[b]naphtho[2,1-d]thiophen-5-ylboronic acid (43.55 g, 156.60 mmol),Pd(PPh₃)₄ (7.24 g, 6.26 mmol), K₂CO₃ (64.93 g, 469.79 mmol), THF (522ml) and water (261 ml) were added to2,4-dichloro-6-phenyl-1,3,5-triazine (35.4 g, 156.60 mmol), and thereaction was carried out in the same manner as in the synthesis methodof Sub 2-2 to obtain 19.58 g (yield: 45%) of the product.

3. Synthesis Example of Final Compound Synthesis Example of 1-6

Sub 1-6 (56.7 g, 164.72 mmol) was placed in a round bottom flask anddissolved in THF (604 ml). Sub 2-3 (67.96 g, 197.66 mmol), Pd(PPh₃)₄(7.61 g, 6.59 mmol), K₂CO₃ (68.30 g, 494.16 mmol) and water (302 ml)were added to the solution and the mixture was stirred under reflux.When the reaction was completed, the reaction product was extracted byusing ether and water. An organic layer was dried over MgSO₄ andconcentrated. Then, the concentrate was separated by a silica gel columnand recrystallized to obtain 64.93 g (yield: 75%) of the product.

Synthesis Example of 1-46

THF (604 mL), Sub 2-22 (88.94 g, 197.66 mmol), Pd(PPh₃)₄ (7.61 g, 6.59mmol), K₂CO₃ (68.30 g, 494.16 mmol) and water (302 mL) were added to Sub1-9 (56.7 g, 164.72 mmol) and the reaction was carried out in the samemanner as in the synthesis method of 1-6 to obtain 81.17 g (yield: 73%)of the product.

Synthesis Example of 1-81

THF (495 mL), Sub 2-65 (70.24 g, 161.88 mmol), Pd(PPh₃)₄ (6.24 g, 5.40mmol), K₂CO₃ (55.93 g, 404.69 mmol) and water (247 mL) were added to Sub1-29 (56.7 g, 134.90 mmol) and the reaction was carried out in the samemanner as in the synthesis method of 1-6 to obtain 59.73 g (yield: 64%)of the product.

Synthesis Example of 1-92

THF (442 mL), Sub 2-6 (45.97 g, 144.65 mmol), Pd(PPh₃)₄ (5.57 g, 4.82mmol), K₂CO₃ (49.98 g, 361.62 mmol) and water (221 mL) were added to Sub1-38 (56.7 g, 120.54 mmol) and the reaction was carried out in the samemanner as in the synthesis method of 1-6 to obtain 65.62 g (yield: 87%)of the product.

Synthesis Example of 1-122

THF (407 mL), Sub 2-6 (42.36 g, 133.31 mmol), Pd(PPh₃)₄ (5.13 g, 4.44mmol), K₂CO₃ (46.06 g, 333.27 mmol) and water (204 mL) were added to Sub1-67 (56.7 g, 111.09 mmol) and the reaction was carried out in the samemanner as in the synthesis method of 1-6 to obtain 59.17 g (yield: 80%)of the product.

Synthesis Example of 1-148

THF (427 mL), Sub 2-6 (44.45 g, 139.87 mmol), Pd(PPh₃)₄ (5.39 g, 4.66mmol), K₂CO₃ (48.33 g, 349.68 mmol) and water (214 mL) were added to Sub1-97 (56.7 g, 116.56 mmol) and the reaction was carried out in the samemanner as in the synthesis method of 1-6 to obtain 62.84 g (yield: 84%)of the product.

Synthesis Example of 1-157

THF (395 mL), Sub 2-6 (41.07 g, 129.24 mmol), Pd(PPh₃)₄ (4.98 g, 4.31mmol), K₂CO₃ (44.66 g, 323.10 mmol) and water (197 mL) were added to Sub1-106 (56.7 g, 107.70 mmol) and the reaction was carried out in the samemanner as in the synthesis method of 1-6 to obtain 59.48 g (yield: 81%)of the product.

The FD-MS values of compounds 1-1 to 1-176 of the present inventionsynthesized by the same method as in Synthesis Example are shown inTable 3 below.

TABLE 3 Compound FD-MS Compound FD-MS 1-1 m/z = 449.15(C₃₁H₁₉N₃O =449.51) 1-2 m/z = 525.18(C₃₇H₂₃N₃O = 525.61) 1-3 m/z = 449.15(C₃₁H₁₉N₃O= 449.51) 1-4 m/z = 449.15(C₃₁H₁₉N₃O = 449.51) 1-5 m/z = 575.2(C₄₁H₂₅N₃O= 575.67) 1-6 m/z = 525.18(C₃₇H₂₃N₃O = 525.61) 1-7 m/z =499.17(C₃₅H₂₁N₃O = 499.57) 1-8 m/z = 677.25(C₄₉H₃₁N₃O = 677.81) 1-9 m/z= 499.17(C₃₅H₂₁N₃O = 499.57) 1-10 m/z = 549.18(C₃₉H₂₃N₃O = 549.63) 1-11m/z = 675.23(C₄₉H₂₉N₃O = 675.79) 1-12 m/z = 575.2(C₄₁H₂₅N₃O = 575.67)1-13 m/z = 701.25(C₅₁H₃₁N₃O = 701.83) 1-14 m/z = 651.23(C₄₇H₂₉N₃O =651.77) 1-15 m/z = 651.23(C₄₇H₂₉N₃O = 651.77) 1-16 m/z = 575.2(C₄₁H₂₅N₃O= 575.67) 1-17 m/z = 549.18(C₃₉H₂₃N₃O = 549.63) 1-18 m/z =549.18(C₃₉H₂₃N₃O = 549.63) 1-19 m/z = 575.2(C₄₁H₂₅N₃O = 575.67) 1-20 m/z= 575.2(C₄₁H₂₅N₃O = 575.67) 1-21 m/z = 575.2(C₄₁H₂₅N₃O = 575.67) 1-22m/z = 555.14(C₃₇H₂₁N₃OS = 555.66) 1-23 m/z = 605.16(C₄₁H₂₃N₃OS = 605.72)1-24 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 1-25 m/z = 631.17(C₄₃H₂₅N₃OS =631.75) 1-26 m/z = 615.19(C₄₃H₂₅N₃O₂ = 615.69) 1-27 m/z =539.16(C₃₇H₂₁N₃O₂ = 539.59) 1-28 m/z = 707.2(C₄₉H₂₉N₃OS = 707.85) 1-29m/z = 707.2(C₄₉H₂₉N₃OS = 707.85) 1-30 m/z = 655.23(C₄₆H₂₉N₃O₂ = 655.76)1-31 m/z = 655.17(C₄₅H₂₅N₃OS = 655.78) 1-32 m/z = 631.17(C₄₃H₂₅N₃OS =631.75) 1-33 m/z = 615.19(C₄₃H₂₅N₃O₂ = 615.69) 1-34 m/z =720.2(C₄₉H₂₈N₄OS = 720.85) 1-35 m/z = 705.21(C₄₉H₂₇N₃O₃ = 705.77) 1-36m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) 1-37 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91)1-38 m/z = 707.2(C₄₉H₂₉N₃OS = 707.85) 1-39 m/z = 707.2(C₄₉H₂₉N₃OS =707.85) 1-40 m/z = 766.27(C₅₅H₃₄N₄O = 766.9) 1-41 m/z =631.17(C₄₃H₂₅N₃OS = 631.75) 1-42 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 1-43m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 1-44 m/z = 707.2(C₄₉H₂₉N₃OS = 707.85)1-45 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 1-46 m/z = 631.17(C₄₃H₂₅N₃OS =631.75) 1-47 m/z = 665.21(C₄₇H₂₇N₃O₂ = 665.75) 1-48 m/z =691.23(C₄₉H₂₉N₃O₂ = 691.79) 1-49 m/z = 665.21(C₄₇H₂₇N₃O₂ = 665.75) 1-50m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) 1-51 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91)1-52 m/z = 715.23(C₅₁H₂₉N₃O₂ = 715.81) 1-53 m/z = 589.18(C₄₁H₂₃N₃O₂ =589.65) 1-54 m/z = 589.18(C₄₁H₂₃N₃O₂ = 589.65) 1-55 m/z =605.16(C₄₁H₂₃N₃OS = 605.72) 1-56 m/z = 589.18(C₄₁H₂₃N₃O₂ = 589.65) 1-57m/z = 605.16(C₄₁H₂₃N₃OS = 605.72) 1-58 m/z = 807.23(C₅₇H₃₃N₃OS = 807.97)1-59 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) 1-60 m/z = 591.18(C₄₁H₂₅N₃S =591.73) 1-61 m/z = 515.15(C₃₅H₂₁N₃S = 515.63) 1-62 m/z =617.19(C₄₃H₂₇N₃S = 617.77) 1-63 m/z = 565.16(C₃₉H₂₃N₃S = 565.69) 1-64m/z = 565.16(C₃₉H₂₃N₃S = 565.69) 1-65 m/z = 581.19(C₄₀H₂₇N₃S = 581.74)1-66 m/z = 555.14(C₃₇H₂₁N₃OS = 555.66) 1-67 m/z = 737.16(C₄₉H₂₇N₃OS₂ =737.9) 1-68 m/z = 518.16(C₃₄H₂₂N₄S = 518.64) 1-69 m/z = 515.15(C₃₅H₂₁N₃S= 515.63) 1-70 m/z = 561.19(C₃₇H₂₇N₃OS = 561.7) 1-71 m/z =630.19(C₄₃H₂₆N₄S = 630.77) 1-72 m/z = 591.18(C₄₁H₂₅N₃S = 591.73) 1-73m/z = 766.27(C₅₅H₃₄N₄O = 766.9) 1-74 m/z = 575.2(C₄₁H₂₅N₃O = 575.67)1-75 m/z = 677.25(C₄₉H₃₁N₃O = 677.81) 1-76 m/z = 707.2(C₄₉H₂₉N₃OS =707.85) 1-77 m/z = 766.27(C₅₅H₃₄N₄O = 766.9) 1-78 m/z = 707.2(C₄₉H₂₉N₃OS= 707.85) 1-79 m/z = 767.26(C₅₅H₃₃N₃O₂ = 767.89) 1-80 m/z =767.26(C₅₅H₃₃N₃O₂ = 767.89) 1-81 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) 1-82m/z = 817.27(C₅₉H₃₅N₃O₂ = 817.95) 1-83 m/z = 741.24(C₅₃H₃₁N₃O₂ = 741.85)1-84 m/z = 741.24(C₅₃H₃₁N₃O₂ = 741.85) 1-85 m/z = 831.23(C₅₉H₃₃N₃OS =831.99) 1-86 m/z = 767.26(C₅₅H₃₃N₃O₂ = 767.89) 1-87 m/z =757.19(C₅₁H₂₇N₅OS = 757.87) 1-88 m/z = 601.22(C₄₃H₂₇N₃O = 601.71) 1-89m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) 1-90 m/z = 625.22(C₄₅H₂₇N₃O = 625.73)1-91 m/z = 625.22(C₄₅H₂₇N₃O = 625.73) 1-92 m/z = 625.22(C₄₅H₂₇N₃O =625.73) 1-93 m/z = 625.22(C₄₅H₂₇N₃O = 625.73) 1-94 m/z =651.23(C₄₇H₂₉N₃O = 651.77) 1-95 m/z = 731.2(C₅₁H₂₉N₃OS = 731.87) 1-96m/z = 833.25(C₅₉H₃₅N₃OS = 834.01) 1-97 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91)1-98 m/z = 867.29(C₆₃H₃₇N₃O₂ = 868.01) 1-99 m/z = 757.22(C₅₃H₃₁N₃OS =757.91) 1-100 m/z = 655.23(C₄₆H₂₉N₃O₂ = 655.76) 1-101 m/z =625.22(C₄₅H₂₇N₃O = 625.73) 1-102 m/z = 625.22(C₄₅H₂₇N₃O = 625.73) 1-103m/z = 625.22(C₄₅H₂₇N₃O = 625.73) 1-104 m/z = 807.23(C₅₇H₃₃N₃OS = 807.97)1-105 m/z = 731.2(C₅₁H₂₉N₃OS = 731.87) 1-106 m/z = 731.2(C₅₁H₂₉N₃OS =731.87) 1-107 m/z = 791.26(C₅₇H₃₃N₃O₂ = 791.91) 1-108 m/z =807.23(C₅₇H₃₃N₃OS = 807.97) 1-109 m/z = 807.23(C₅₇H₃₃N₃OS = 807.97)1-110 m/z = 575.20(C₄₁H₂₅N₃O = 575.67) 1-111 m/z = 867.29(C₆₃H₃₇N₃O₂ =868.01) 1-112 m/z = 807.23(C₅₇H₃₃N₃OS = 807.97) 1-113 m/z =777.28(C₅₇H₃₅N₃O = 777.93) 1-114 m/z = 803.29(C₅₉H₃₇N₃O = 803.97) 1-115m/z = 632.26(C₄₅H₂₀D₇N₃O = 632.77) 1-116 m/z = 715.23(C₅₁H₂₉N₃O₂ =715.81) 1-117 m/z = 883.27(C₆₃H₃₇N₃OS = 884.07) 1-118 m/z =833.25(C₅₉H₃₅N₃OS = 834.01) 1-119 m/z = 942.34(C₆₉H₄₂N₄O = 943.12) 1-120m/z = 701.25(C₅₁H₃₁N₃O = 701.83) 1-121 m/z = 615.19(C₄₃H₂₅N₃O₂ = 615.69)1-122 m/z = 665.21(C₄₇H₂₇N₃O₂ = 665.75) 1-123 m/z = 681.19(C₄₇H₂₇N₃OS =681.81) 1-124 m/z = 715.23(C₅₁H₂₉N₃O₂ = 715.81) 1-125 m/z =691.23(C₄₉H₂₉N₃O₂ = 691.79) 1-126 m/z = 691.23(C₄₉H₂₀N₃O₂ = 691.79)1-128 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) 1-129 m/z = 757.22(C₅₃H₃₁N₃OS =757.91) 1-130 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) 1-131 m/z =817.27(C₅₉H₃₅N₃O₂ = 817.95) 1-132 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79)1-133 m/z = 781.24(C₅₅H₃₁N₃O₃ = 781.87) 1-134 m/z = 797.21(C₅₅H₃₁N₃O₂S =797.93) 1-136 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) 1-137 m/z =691.23(C₄₉H₂₉N₃O₂ = 691.79) 1-138 m/z = 780.25(C₅₅H₃₂N₄O₂ = 780.89)1-139 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) 1-140 m/z = 781.18(C₄₉H₂₄F₅N₃O₂= 781.74) 1-141 m/z = 732.29(C₅₃H₂₈D₅N₃O = 732.9) 1-142 m/z =793.27(C₅₇H₃₅N₃O₂ = 793.93) 1-143 m/z = 651.23(C₄₇H₂₉N₃O = 651.77) 1-144m/z = 755.26(C₅₄H₃₃N₃O₂ = 755.88) 1-145 m/z = 591.18(C₄₁H₂₅N₃S = 591.73)1-146 m/z = 617.19(C₄₃H₂₇N₃S = 617.77) 1-147 m/z = 707.24(C₅₀H₃₃N₃S =707.9) 1-148 m/z = 641.19(C₄₅H₂₇N₃S = 641.79) 1-149 m/z =641.19(C₄₅H₂₇N₃S = 641.79) 1-150 m/z = 641.19(C₄₅H₂₇N₃S = 641.79) 1-151m/z = 793.26(C₅₇H₃₅N₃S = 793.99) 1-152 m/z = 641.19(C₄₅H₂₇N₃S = 641.79)1-153 m/z = 667.21(C₄₇H₂₉N₃S = 667.83) 1-154 m/z = 823.21(C₅₇H₃₃N₃S₂ =824.03) 1-155 m/z = 883.27(C₆₃H₃₇N₃OS = 884.07) 1-156 m/z =747.18(C₅₁H₂₉N₃S₂ = 747.93) 1-157 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81)1-158 m/z = 697.16(C₄₇H₂₇N₃S₂ = 697.87) 1-159 m/z = 731.2(C₅₁H₂₉N₃OS =731.87) 1-160 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 1-162 m/z =737.16(C₄₉H₂₇N₃OS₂ = 737.9) 1-163 m/z = 707.2(C₄₉H₂₉N₃OS = 707.85) 1-164m/z = 707.2(C₄₉H₂₉N₃OS = 707.85) 1-165 m/z = 747.18(C₅₁H₂₉N₃S₂ = 747.93)1-166 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81 ) 1-167 m/z = 731.2(C₅₁H₂₉N₃OS =731.87) 1-168 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 1-169 m/z =731.2(C₅₁H₂₉N₃OS = 731.87) 1-170 m/z = 721.18(C₄₉H₂₇N₃O₂S = 721.83)1-171 m/z = 691.23(C₄₀H₂₉N₃O₂ = 691.79) 1-172 m/z = 691.23(C₄₉H₂₉N₃O₂ =691.79) 1-173 m/z = 741.24(C₅₃H₃₁N₃O₂ = 741.85) 1-174 m/z =807.23(C₅₇H₃₃N₃OS = 807.97) 1-175 m/z = 799.21(C₅₅H₃₃N₃S₂ = 800.01)1-176 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91)

[Synthesis Example 2] Formula 2

The compound (Final product 2) represented by Formula 2 of the presentinvention may be prepared by reacting Sub 3 and Sub 4 as shown inReaction Scheme 4 below, but is not limited thereto.

<Reaction Scheme 4>

1. Exemplary Compounds and Synthesis Examples of Sub 3

The compounds belonging to Sub 3 of Reaction Scheme 4 are as follows,but are not limited thereto.

The FD-MS values of the compounds belonging to Sub 3 are shown in Table4 below.

TABLE 4 Compound FD-MS Compound FD-MS Sub 3-1 m/z = 332.13(C₂₄H₁₆N₂ =332.41) Sub 3-2 m/z = 273.06(C₁₈H₁₁NS = 273.35) Sub 3-3 m/z =257.08(C₁₈H₁₁NO = 257.29) Sub 3-4 m/z = 283.14(C₂₁H₁₇N = 283.37) Sub 3-5m/z = 257.08(C₁₈H₁₁NO = 257.29) Sub 3-6 m/z = 283.14(C₂₁H₁₇N = 283.37)Sub 3-7 m/z = 332.13(C₂₄H₁₆N₂ = 332.41) Sub 3-8 m/z = 273.06(C₁₈H₁₁NS =273.35) Sub 3-9 m/z = 257.08(C₁₈H₁₁NO = 257.29) Sub 3-10 m/z =283.14(C₂₁H₁₇N = 283.37) Sub 3-11 m/z = 332.13(C₂₄H₁₆N₂ = 332.41) Sub3-12 m/z = 332.13(C₂₄H₁₆N₂ = 332.41) Sub 3-13 m/z = 257.08(C₁₈H₁₁NO =257.29) Sub 3-14 m/z = 283.14(C₂₁H₁₇N = 283.37) Sub 3-15 m/z =358.15(C₂₆H₁₈N₂ = 358.44) Sub 3-16 m/z = 530.15(C₃₆H₂₂N₂OS = 530.65) Sub3-17 m/z = 333.12(C₂₄H₁₅NO = 333.39) Sub 3-18 m/z = 408.16(C₃₀H₂₀N₂ =408.5) Sub 3-19 m/z = 407.17(C₃₁H₂₁N = 407.52) Sub 3-20 m/z =422.08(C₂₄H₁₁F₅N₂ = 422.36) Sub 3-21 m/z = 501.16(C₃₆H₂₃NS = 501.65) Sub3-22 m/z = 537.18(C₃₈H₂₃N₃O = 537.62) Sub 3-23 m/z = 313.15(C₂₂H₁₉NO =313.4) Sub 3-24 m/z = 408.16(C₃₀H₂₀N₂ = 408.5) Sub 3-25 m/z =333.12(C₂₄H₁₅NO = 333.39) Sub 3-26 m/z = 359.17(C₂₇H₂₁N = 359.47) Sub3-27 m/z = 349.09(C₂₄H₁₅NS = 349.45) Sub 3-28 m/z = 349.09(C₂₄H₁₅N₅ =349.45) Sub 3-29 m/z = 333.12(C₂₄H₁₅NO = 333.39) Sub 3-30 m/z =540.22(C₃₉H₂₈N₂O = 540.67) Sub 3-31 m/z = 435.2(C₃₃H₂₅N = 435.57) Sub3-32 m/z = 408.16(C₃₀H₂₀N₂ = 408.5) Sub 3-33 m/z = 349.09(C₂₄H₁₅NS =349.45) Sub 3-34 m/z = 333.12(C₂₄H₁₅NO = 333.39) Sub 3-35 m/z =497.21(C₃₈H₂₇N = 497.64) Sub 3-36 m/z = 382.15(C₂₈H₁₈N₂ = 382.47) Sub3-37 m/z = 382.15(C₂₈H₁₈N₂ = 382.47) Sub 3-38 m/z = 382.15(C₂₈H₁₈N₂ =382.47) Sub 3-39 m/z = 458.18(C₃₄H₂₂N₂ = 458.56) Sub 3-40 m/z =382.15(C₂₈H₁₈N₂ = 382.47) Sub 3-41 m/z = 382.15(C₂₈H₁₈N₂ = 382.47) Sub3-42 m/z = 458.18(C₃₄H₂₂N₂ = 458.56) Sub 3-43 m/z = 508.19(C₃₈H₂₄N₂ =508.62) Sub 3-44 m/z = 458.18(C₃₄H₂₂N₂ = 458.56) Sub 3-45 m/z =382.15(C₂₈H₁₈N₂ = 382.47) Sub 3-46 m/z = 508.19(C₃₈H₂₄N₂ = 508.62) Sub3-47 m/z = 382.15(C₂₈H₁₈N₂ = 382.47) Sub 3-48 m/z = 382.15(C₂₈H₁₈N₂ =382.47) Sub 3-49 m/z = 323.08(C₂₂H₁₃NS = 323.41) Sub 3-50 m/z =399.11(C₂₈H₁₇NS = 399.51) Sub 3-51 m/z = 399.11(C₂₈H₁₇NS = 399.51) Sub3-52 m/z = 399.11(C₂₈H₁₇NS = 399.51) Sub 3-53 m/z = 373.09(C₂₆H₁₅NS =373.47) Sub 3-54 m/z = 373.09(C₂₆H₁₅NS = 373.47) Sub 3-55 m/z =323.08(C₂₂H₁₃NS = 323.41) Sub 3-56 m/z = 323.08(C₂₂H₁₃NS = 323.41) Sub3-57 m/z = 323.08(C₂₂H₁₃NS = 323.41) Sub 3-58 m/z = 323.08(C₂₂H₁₃NS =323.41) Sub 3-59 m/z = 357.12(C₂₆H₁₅NO = 357.41) Sub 3-60 m/z =307.1(C₂₂H₁₃NO = 307.35) Sub 3-61 m/z = 333.15(C₂₅H₁₉N = 333.43) Sub3-62 m/z = 455.17(C₃₅H₂₁N = 455.56) Sub 3-63 m/z = 323.08(C₂₂H₁₃NS =323.41) Sub 3-64 m/z = 382.15(C₂₈H₁₈N₂ = 382.47) Sub 3-65 m/z =445.18(C₃₄H₂₃N = 445.57) Sub 3-66 m/z = 485.21(C₃₇H₂₇N = 485.63) Sub3-67 m/z = 409.18(C₃₁H₂₃N = 409.53) Sub 3-68 m/z = 383.13(C₂₈H₁₇NO =383.45) Sub 3-69 m/z = 651.2(C₄₈H₂₉NS = 651.83) Sub 3-70 m/z =497.19(C₃₆H₂₃N₃ = 497.6) Sub 3-71 m/z = 408.16(C₃₀H₂₀N₂ = 408.50)

1. Synthesis Example of Sub 3

Sub 3 may be synthesized by the reaction route of the following ReactionScheme 4-1, but are not limited thereto.

Synthesis Example of Sub 3-7

(1) Synthesis of Sub 3-b-7

Sub 3-a-7 (40 g, 124.1 mmol) was dissolved in DMF (600 ml), andbis(pinacolato)diboron (40.9 g, 161.4 mmol), KOAc (36.6 g, 372.4 mmol),PdCl₂(dppf) (4.5 g, 6.2 mmol) were added to the solution. Then, themixture was stirred at 120° C. When the reaction was completed, DMF wasremoved through distillation and the reaction product was extracted withCH₂Cl₂ and water. An organic layer was dried over MgSO₄ andconcentrated. Then, the concentrate was separated by a silica gel columnand recrystallized to obtain 35.3 g (yield: 77%) of Sub 3-b-7.

(2) Synthesis of Sub 3-d-7.

Sub 3-b-7 (35 g, 94.8 mmol) was dissolved in THF (600 mL), and Sub 3-c-1(23 g, 113.7 mmol), K₂CO₃ (39.3 g, 284.34 mmol), Pd(PPh₃)₄ (5.5 g, 4.74mmol) and water (300 mL) were added to the solution. Then, the mixturewas stirred at 80° C. When the reaction was completed, the reactionproduct was extracted with CH₂Cl₂ and water. An organic layer was driedover MgSO₄ and concentrated. Then, the concentrate was separated by asilica gel column and recrystallized to obtain 23.5 g (yield: 68%) ofSub 3-d-7.

(3) Synthesis of Sub 3-7

Sub 3-d-7 (15 g, 41.2 mmol) was dissolved in o-dichlorobenzene (450 mL),and triphenylphosphine (27 g, 102.9 mmol) was added to the solution.Then, the mixture was stirred at 200° C. When the reaction wascompleted, o-dichlorobenzene was removed through distillation and thereaction product was extracted with CH₂Cl₂ and water. An organic layerwas dried over MgSO₄ and concentrated. Then, the concentrate wasseparated by a silica gel column and recrystallized to obtain Sub 3-7(8.35 g, yield: 61%).

Synthesis Example of Sub 3-12

(1) Synthesis of Sub 3-b-12

Sub 3-a-12 (35 g, 108.6 mmol) was dissolved in DMF (540 mL)) andbis(pinacolato)diboron (35.9 g, 141.2 mmol), KOAc (32 g, 325.9 mmol),PdCl₂(dppf) (4 g, 5.43 mmol) were added to the solution. Then, thereaction was carried out in the same manner as in the synthesis methodof Sub 3-b-7 to obtain 29.7 g (yield: 74%) of Sub 3-b-12.

(2) Synthesis of Sub 3-d-12

Sub 3-b-12 (25 g, 67.7 mmol) was dissolved in THF (420 mL) and Sub 3-c-1(16.4 g, 81.2 mmol), K₂CO₃ (28.1 g, 203.1 mmol), Pd(PPh₃)₄ (3.9 g, 3.4mmol) and water (210 mL) were added to the solution. Then, the reactionwas carried out in the same manner as in the synthesis method of Sub3-d-7 to obtain 17.5 g (yield: 71%) of Sub 3-d-12.

(3) Synthesis of Sub 3-12

Sub 3-d-12 (10 g, 27.44 mmol) was dissolved in o-dichlorobenzene (270mL) and triphenylphosphine (18 g, 68.6 mmol) was added to the solution.Then, the reaction was carried out in the same manner as in thesynthesis method of Sub 3-7 to obtain Sub 3-12 (5.4 g, yield: 59%).

Synthesis Example of Sub 3-36

(1) Synthesis of Sub 3-b-36

Sub 3-a-36 (28 g, 86.9 mmol) was dissolved in DMF (430 mL) andbis(pinacolato)diboron (28.7 g, 112.9 mmol), KOAc (25.6 g, 260.7 mmol),PdCl₂(dppf) (3.2 g, 4.34 mmol) were added to the solution. Then, thereaction was carried out in the same manner as in the synthesis methodof Sub 3-b-7 to obtain 26.3 g (yield: 82%) of Sub 3-b-36.

(2) Synthesis of Sub 3-d-36

Sub 3-b-36 (25 g, 67.7 mmol) was dissolved in THF (450 mL) and Sub 3-c-2(16.4 g, 81.2 mmol), K₂CO₃ (28.1 g, 203.1 mmol), Pd(PPh₃)₄ (3.9 g, 3.4mmol) and water (225 mL) were added to the solution. Then, the reactionwas carried out in the same manner as in the synthesis method of Sub3-d-7 to obtain 20.76 g (yield: 74%) of Sub 3-d-36.

(3) Synthesis of Sub 3-36

Sub 3-d-36 (15 g, 36.19 mmol) was dissolved in o-dichlorobenzene (350mL) and triphenylphosphine (23.7 g, 90.5 mmol) was added to thesolution. Then, the reaction was carried out in the same manner as inthe synthesis method of Sub 3-7 to obtain Sub 3-36 (5.8 g, yield: 42%).

Synthesis Example of Sub 3-53

(1) Synthesis of Sub 3-b-53

Sub 3-a-53 (40 g, 127.71 mmol) was dissolved in DMF (600 mL) andbis(pinacolato)diboron (42.2 g, 166.02 mol), KOAc (37.6 g, 383.1 mmol),PdCl₂(dppf) (4.7 g, 6.4 mmol) were added to the solution. Then, thereaction was carried out in the same manner as in the synthesis methodof Sub 3-b-7 to obtain 38.7 g (yield: 84%) of Sub 3-b-53.

(2) Synthesis of Sub 3-d-53

Sub 3-b-53 (35 g, 97.2 mmol) was dissolved in THF (600 mL) and Sub 3-c-3(29.4 g, 116.6 mmol), K₂CO₃ (40.3 g, 291.4 mmol), Pd(PPh₃)₄ (5.6 g, 4.9mmol) and water (300 mL) were added to the solution. Then, the reactionwas carried out in the same manner as in the synthesis method of Sub3-d-7 to obtain 30.7 g (yield: 78%) of Sub 3-d-53.

(3) Synthesis of Sub 3-53

Sub 3-d-53 (15 g, 37 mmol) was dissolved in o-dichlorobenzene (350 mL)and triphenylphosphine (24.3 g, 92.5 mmol) was added to the solution.Then, the reaction was carried out in the same manner as in thesynthesis method of Sub 3-7 to obtain Sub 3-53 (8.7 g, yield: 63%).

Synthesis Example of Sub 3-71

(1) Synthesis of Sub 3-b-71

Sub 3-a-79 (28 g, 86.9 mmol) was dissolved in DMF (430 mL) andbis(pinacolato)diboron (28.7 g, 113 mol), KOAc (25.6 g, 260.7 mmol),PdCl₂(dppf) (3.2 g, 4.3 mmol) were added to the solution. Then, thereaction was carried out in the same manner as in the synthesis methodof Sub 3-b-7 to obtain 28.2 g (yield: 88%) of Sub 3-b-71.

(2) Synthesis of Sub 3-d-71

Sub 3-b-2 (25 g, 67.7 mmol) was dissolved in THF (450 mL) and Sub 3-c-1(22.6 g, 81.2 mmol), K₂CO₃ (28.1 g, 203.1 mmol), Pd(PPh₃)₄ (3.9 g, 3.4mmol) and water (220 mL) were added to the solution. Then, the reactionwas carried out in the same manner as in the synthesis method of Sub3-d-7 to obtain 21.8 g (yield: 73%) of Sub 3-d-71.

(3) Synthesis of Sub 3-71

Sub 3-d-79 (20 g, 45.4 mmol) was dissolved in o-dichlorobenzene (420 mL)and triphenylphosphine (29.8 g, 113.5 mmol) was added to the solution.Then, the reaction was carried out in the same manner as in thesynthesis method of Sub 3-7 to obtain Sub 3-71 (7.8 g, yield: 42%).

2. Exemplary Compounds of Sub 4

The compounds belonging to Sub 4 of Reaction Scheme 4 are as follows,but are not limited thereto.

The ED-MS values of the compounds belonging to Sub 4 are shown in Table5 below.

TABLE 5 Compound FD-MS Compound FD-MS Sub 4-1 m/z = 155.96(C₆H₅Br =157.01) Sub 4-2 m/z = 231.99(C₁₂H₉Br = 233.11) Sub 4-3 m/z =205.97(C₁₀H₇Br = 207.07) Sub 4-4 m/z = 231.99(C₁₂H₉Br = 233.11) Sub 4-5m/z = 282(C₁₆H₁₁Br = 283.17) Sub 4-6 miz = 255.99(C₁₄H₉Br = 257.13) Sub4-7 m/z = 332.02(C₂₀H₁₃Br = 333.23) Sub 4-8 m/z = 237.02(C₁₂F₁₄D₅Br =238.14) Sub 4-9 m/z = 308.02(C₁₈H₁₃Br = 309.21) Sub 4-10 m/z =282(C₁₆H₁₁Br = 283.17) Sub 4-11 m/z = 205.97(C₁₀H₇Br = 207.07) Sub 4-12m/z = 282(C₁₆H₁₁Br = 283.17) Sub 4-13 m/z = 287.04(C₁₆H₆D₅Br = 288.2)Sub 4-14 m/z = 173.95(C₆H₄BrF = 175) Sub 4-15 m/z = 282(C₁₆H₁₁Br =283.17) Sub 4-16 m/z = 308.02(C₁₈H₁₃Br = 309.21) Sub 4-17 m/z =432.05(C₂₈H₁₇Br = 433.35) Sub 4-18 m/z = 358.04(C₂₂H₁₅Br = 359.27) Sub4-19 m/z = 332.02(C₂₀H₁₃Br = 333.23) Sub 4-20 m/z = 308.02(C₁₈H₁₃Br =309.21) Sub 4-21 m/z = 231.99(C₁₂H₉Br = 233.11) Sub 4-22 m/z =308.02(C₁₈H₁₃Br = 309.21) Sub 4-23 m/z = 243.99(C₁₃H₉Br = 245.12) Sub4-24 m/z = 321.94(C₁₂H₄BrF₅ = 323.06) Sub 4-25 m/z = 113(C₅H₄ClN =113.54) Sub 4-26 m/z = 113(C₅H₄ClN = 113.54) Sub 4-27 m/z = 114(C₄H₃ClN₂= 114.53) Sub 4-28 m/z = 114(C₄H₃ClN₂ = 114.53) Sub 4-29 m/z =266.06(C₁₆H₁₁ClN₂ = 266.73) Sub 4-30 m/z = 267.06(C₁₅H₁₀ClN₃ = 267.72)Sub 4-31 m/z = 317.07(C₁₉H₁₂ClN3 = 317.78) Sub 4-32 m/z =367.09(C₂₃H₁₄ClN₃ = 367.84) Sub 4-33 m/z = 240.05(C₁₄H₉ClN₂ = 240.69)Sub 4-34 m/z = 240.05(C₁₄H₉ClN₂ = 240.69) Sub 4-35 m/z =290.06(C₁₈H₁₁ClN₂ = 290.75) Sub 4-36 m/z = 290.06(C₁₈H₁₁ClN₂ = 290.75)Sub 4-37 m/z = 290.06(C₁₈H₁₁ClN₂ = 290.75) Sub 4-38 m/z =254.06(C₁₅H₁₁ClN₂ = 254.72) Sub 4-39 m/z = 290.06(C₁₈H₁₁ClN₂ = 290.75)Sub 4-40 m/z = 240.05(C₁₄H₉ClN₂ = 240.69) Sub 4-41 m/z =290.06(C₁₈H₁₁ClN₂ = 290.75) Sub 4-42 m/z = 316.08(C₂₀H₁₃ClN₂ = 316.79)Sub 4-43 m/z = 372.05(C₂₂H₁₃ClN₂S = 372.87) Sub 4-44 m/z =330.06(C₂₀H₁₁ClN₂O = 330.77) Sub 4-45 m/z = 296.02(C₁₆H₉ClN₂S = 296.77)Sub 4-46 m/z = 296.02(C₁₆H₉ClN₂S = 296.77) Sub 4-47 m/z =280.04(C₁₆H₉ClN₂O = 280.71) Sub 4-48 m/z = 305.04(C₁₇H₈ClN₃O = 305.72)Sub 4-49 m/z = 402.01(C₂₂H₁₁ClN₂S₂ = 402.91) Sub 4-50 m/z =513.07(C₃₁H₁₆ClN₃OS = 514) Sub 4-51 m/z = 396.1(C₂₅H₁₇ClN₂O = 396.87)Sub 4-52 m/z = 290.06(C₁₈H₁₁ClN₂ = 290.75) Sub 4-53 m/z =340.08(C₂₂H₁₃ClN₂ = 340.81) Sub 4-54 m/z = 383.08(C₂₃H₁₄ClN₃O = 383.84)Sub 4-55 m/z = 398.06(C₂₄H₁₅ClN₂S = 398.91) Sub 4-56 m/z =431.08(C₂₇H₁₄ClN₃O = 431.88) Sub 4-57 m/z = 406.09(C₂₆H₁₅ClN₂O = 406.87)Sub 4-58 m/z = 387.04(C₂₁H₁₄BrN₃ = 388.27) Sub 4-59 m/z =360.03(C₂₀H₁₃BrN₂ = 361.24) Sub 4-60 m/z = 360.03(C₂₀H₁₃BrN₂ = 361.24)Sub 4-61 m/z = 416(C₂₂H₁₃BrN₂S = 417.32) Sub 4-62 m/z =400.02(C₂₂H₁₃BrN₂O = 401.26) Sub 4-63 m/z = 428.03(C₂₄H₁₄BrFN₂ = 429.29)Sub 4-64 m/z = 410.04(C₂₄H₁₅BrN₂ = 411.3) Sub 4-65 m/z =437.05(C₂₅H₁₆BrN₃ = 438.33) Sub 4-66 m/z = 295.98(C₁₆H₉BrO = 297.15) Sub4-67 m/z = 311.96(C₁₆H₉BrS = 313.21) Sub 4-68 m/z = 387.99(C₂₂H₁₃BrS =389.31) Sub 4-74 m/z = 372.01(C₂₂H₁₃BrO = 373.25) Sub 4-75 m/z =422.03(C₂₆H₁₅BrO = 423.31)

3. Synthesis Example of Final Compound Synthesis Example of 2-36

Sub 3-71 (65 g, 159.12 mmol) was dissolved in toluene (800 mL), and Sub4-4 (37.09 g, 159.12 mmol), Pd₂(dba)₃ (4.37 g, 4.77 mmol), P(t-Bu)₃(3.22 g, 15.91 mmol), NaOt-Bu (30.59 g, 318.24 mmol) were added to thesolution. Then, the mixture was stirred at 120° C. When the reaction wascompleted, the reaction product was extracted with CH₂Cl₂ and water. Anorganic layer was dried over MgSO₄ and concentrated. Then, theconcentrate was separated by a silica gel column and recrystallized toobtain 74.94 g (yield: 84%) of the product 2-36.

Synthesis Example of 2-105

Sub 3-47 (65 g, 169.95 mmol) was dissolved in toluene (850 mL) and Sub4-4 (39.62 g, 169.95 mmol), Pd₂(dba)₃ (4.67 g, 5.10 mmol), P(t-Bu)₃(3.44 g, 16.99 mmol), NaOt-Bu (32.67 g, 339.90 mmol) were added to thesolution. Then, the reaction was carried out in the same manner as inthe synthesis method of 2-36 to obtain 74.51 g (yield: 82%) of theproduct 2-105.

Synthesis Example of 2-106

Sub 3-48 (65 g, 169.95 mmol) was dissolved in toluene (850 mL) and Sub4-4 (39.62 g, 169.95 mmol), Pd₂(dba)₃ (4.67 g, 5.10 mmol), P(t-Bu)₃(3.44 g, 16.99 mmol), NaOt-Bu (32.67 g, 339.90 mmol) were added to thesolution. Then, the reaction was carried out in the same manner as inthe synthesis method of 2-36 to obtain 68.15 g (yield: 75%) of theproduct 2-106.

Synthesis Example of 2-110

Sub 3-52 (65 g, 162.70 mmol) was dissolved in toluene (800 mL) and Sub4-3 (33.69 g, 162.70 mmol), Pd₂(dba)₃ (4.47 g, 4.88 mmol), P(t-Bu)₃(3.29 g, 16.27 mmol), NaOt-Bu (31.27 g, 325.40 mmol) were added to thesolution. Then, the reaction was carried out in the same manner as inthe synthesis method of 2-36 to obtain 69.28 g (yield: 81%) of theproduct 2-110.

Synthesis Example of 2-112

Sub 3-54 (65 g, 174.04 mmol) was dissolved in toluene (850 mL) and Sub4-3 (36.04 g, 174.04 mmol), Pd₂(dba)₃ (4.78 g, 5.22 mmol), P(t-Bu)₃(3.52 g, 17.40 mmol), NaOt-Bu (33.45 g, 348.09 mmol) were added to thesolution. Then, the reaction was carried out in the same manner as inthe synthesis method of 2-36 to obtain 68.70 g (yield: 79%) of theproduct 2-112.

Synthesis Example of 2-113

Sub 3-70 (65 g, 130.63 mmol) was dissolved in toluene (650 mL) and Sub4-1 (20.51 g, 130.63 mmol), Pd₂(dba)₃ (3.59 g, 3.92 mmol), P(t-Bu)₃(2.64 g, 13.06 mmol), NaOt-Bu (25.11 g, 261.25 mmol) were added to thesolution. Then, the reaction was carried out in the same manner as inthe synthesis method of 2-36 to obtain 56.95 g (yield: 76%) of theproduct 2-113.

Synthesis Example of 2-129

Sub 3-7 (65 g, 195.54 mmol) was dissolved in toluene (950 mL) and Sub4-66 (58.11 g, 195.54 mmol), Pd₂(dba)₃ (5.37 g, 5.87 mmol), P(t-Bu)₃(39.56 g, 195.54 mmol), NaOt-Bu (37.59 g, 391.08 mmol) were added to thesolution. Then, the reaction was carried out in the same manner as inthe synthesis method of 2-36 to obtain 85.83 g (yield: 80%) of theproduct 2-129.

The FD-MS values of the compounds 2-1 to 2-166 of the present inventionsynthesized by the above synthesis method are shown in Table 6 below.

TABLE 6 Compound FD-MS Compound FD-MS 2-1 m/z = 408.16(C₃₀H₂₀N₂ = 408.5)2-2 m/z = 435.17(C₃₁H₂₁N₃ = 435.53) 2-3 m/z = 410.15(C₂₈H₁₈N₄ = 410.48)2-4 m/z = 536.2(C₃₈H₂₄N₄ = 536.64) 2-5 m/z = 586.22(C₄₂H₂₆N₄ = 586.7)2-6 m/z = 536.2(C₃₈H₂₄N₄ = 536.64) 2-7 m/z = 563.21(C₃₉H₂₅N₅ = 563.66)2-8 m/z = 592.17(C₄₀H₂₄N₄S = 592.72) 2-9 m/z = 491.15(C₃₃H₂₁N₃S =491.61) 2-10 m/z = 527.15(C₃₆H₂₁N₃S = 527.65) 2-11 m/z =533.1(C₃₄H₁₉N₃S₂ = 533.67) 2-12 m/z = 580.17(C₃₉H₂₄N₄S = 580.71) 2-13m/z = 504.14(C₃₃H₂₀N₄S = 504.61) 2-14 m/z = 477.13(C₃₂H₁₉N₃S = 477.59)2-15 m/z = 477.13(C₃₂H₁₉N₃S = 477.59) 2-16 m/z = 425.12(C₃₀H₁₉NS =425.55) 2-17 m/z = 734.18(C₄₉H₂₆N₄O₂S = 734.83) 2-18 m/z =577.18(C₄₀H₂₃N₃O₂ = 577.64) 2-19 m/z = 517.12(C₃₄H₁₉N₃OS = 517.61) 2-20m/z = 606.18(C₄₂H₂₆N₂OS = 606.74) 2-21 m/z = 488.16(C₃₃H₂₀N₄O = 488.55)2-22 m/z = 459.16(C₃₄H₂₁NO = 459.55) 2-23 m/z = 517.12(C₃₄H₁₉N₃OS =517.61) 2-24 m/z = 461.15(C₃₂H₁₉N₃O = 461.52) 2-25 m/z = 552.2(C₃₈H₂₄N₄O= 552.64) 2-26 m/z = 435.2(C₃₃H₂₅N = 435.57) 2-27 m/z = 527.2(C₃₇H₂₅N₃O= 527.63) 2-28 m/z = 513.22(C₃₇H₂₇N₃ = 513.64) 2-29 m/z =534.21(C₄₀H₂₈N₂ = 534.66) 2-30 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) 2-31 m/z= 586.22(C₄₂H₂₆N₄ = 586.7) 2-32 m/z = 536.2(C₃₈H₂₄N₄ = 536.64) 2-33 m/z= 592.17(C₄₀H₂₄N₄S = 592.72) 2-34 m/z = 586.22(C₄₂H₂₆N₄ = 586.7) 2-35m/z = 563.21(C₃₉H₂₅N₅ = 563.66) 2-36 m/z = 560.23(C₄₂H₂₈N₂ = 560.7) 2-37m/z = 527.15(C₃₆H₂₁N₃S = 527.65) 2-38 m/z = 577.19(C₄₂H₂₇NS = 577.75)2-39 m/z = 553.16(C₃₈H₂₃N₃S = 553.68) 2-40 m/z = 639.09(C₄₀H₂₁N₃S₃ =639.81) 2-41 m/z = 527.15(C₃₆H₂₁N₃S = 527.65) 2-42 m/z =527.15(C₃₆H₂₁N₃S = 527.65) 2-43 m/z = 504.14(C₃₃H₂₀N₄S = 504.61) 2-44m/z = 351.08(C₂₂H₁₃N₃S = 351.43) 2-45 m/z = 511.17(C₃₈H₂₁N₃O = 511.58)2-46 m/z = 613.22(C₄₄H₂₇N₃O = 613.72) 2-47 m/z = 587.2(C₄₂H₂₅N₃O =587.68) 2-48 m/z = 538.18(C₃₇H₂₂N₄O = 538.61) 2-49 m/z =517.12(C₃₄H₁₉N₃OS = 517.61) 2-50 m/z = 511.17(C₃₆H₂₁N₃O = 511.58) 2-51m/z = 501.15(C₃₄H₁₉N₃O₂ = 501.55) 2-52 m/z = 461.15(C₃₂H₁₉N₃O = 461.52)2-53 m/z = 459.2(C₃₅H₂₅N = 459.59) 2-54 m/z = 649.22(C₄₄H₃₁N₃OS =649.81) 2-55 m/z = 630.24(C₄₄H₃₀N₄O = 630.75) 2-56 m/z =645.22(C₄₅H₃₁N₃S = 645.82) 2-57 m/z = 692.26(C₄₉H₃₂N₄O = 692.82) 2-58m/z = 680.24(C₄₈H₂₉FN₄ = 680.79) 2-59 m/z = 626.21(C₄₄H₂₈N₄O = 626.72)2-60 m/z = 484.19(C₃₆H₂₄N₂ = 484.6) 2-61 m/z = 586.22(C₄₂H₂₈N₄ = 586.7)2-62 m/z = 536.2(C₃₆H₂₄N₄ = 536.64) 2-63 m/z = 590.18(C₄₂H₂₆N₂S =590.74) 2-64 m/z = 484.19(C₃₆H₂₄N₂ = 484.6) 2-65 m/z = 477.13(C₃₂H₁₉N₃S= 477.59) 2-66 m/z = 525.16(C₃₈H₂₃NS = 525.67) 2-67 m/z =533.1(C₃₄H₁₉N₃S₂ = 533.67) 2-68 m/z = 517.12(C₃₄H₁₉N₃OS = 517.61) 2-69m/z = 414.18(C₃₀H₁₄D₅NO = 414.52) 2-70 m/z = 511.17(C₃₆H₂₁N₃O = 511.58)2-71 m/z = 537.18(C₃₈H₂₃N₃O = 537.62) 2-72 m/z = 561.21(C₄₂H₂₇NO =561.68) 2-73 m/z = 653.25(C₄₇H₃₁N₃O = 653.79) 2-74 m/z = 485.21(C₃₇H₂₇N= 485.63) 2-75 m/z = 586.22(C₄₂H₂₆N₄ = 586.7) 2-76 m/z = 563.21(C₃₉H₂₅N₅= 563.66) 2-77 m/z = 586.22(C₄₂H₂₆N₄ = 586.7) 2-78 m/z = 663.24(C₄₇H₂₉N₅= 663.78) 2-79 m/z = 551.17(C₄₀H₂₅NS = 551.71) 2-80 m/z =464.19(C₃₄H₁₆D₅NO = 464.58) 2-81 m/z = 652.19(C₄₅H₂₄N₄O₂ = 652.71) 2-82m/z = 593.16(C₄₀H₂₃N₃OS = 593.7) 2-83 m/z = 609.25(C₄₇H₃₁N = 609.77)2-84 m/z = 624.16(C₄₀H₂₁F₅N₂ = 624.61) 2-85 m/z = 577.19(C₄₂H₂₇NS =577.75) 2-86 m/z = 611.22(C₄₆H₂₉NO = 611.74) 2-87 m/z =634.24(C₄₅H₃₁FN₂O = 634.75) 2-88 m/z = 635.26(C₄₉H₃₃N = 635.81) 2-89 m/z= 561.25(C₄₃H₃₁N = 561.73) 2-90 m/z = 560.23(C₄₂H₂₈N₂ = 560.7) 2-91 m/z= 601.19(C₄₄H₂₇NS = 601.77) 2-92 m/z = 575.13(C₃₆H₁₈F₅NO = 575.54) 2-93m/z = 623.26(C₄₈H₃₃N = 623.8) 2-94 m/z = 458.18(C₃₄H₂₂N₂ = 458.56) 2-95m/z = 534.21(C₄₀H₂₆N₂ = 534.66) 2-96 m/z = 584.23(C₄₄H₂₈N₂ = 584.72)2-97 m/z = 534.21(C₄₀H₂₆N₂ = 534.66) 2-98 m/z = 610.24(C₄₆H₃₀N₂ =610.76) 2-99 m/z = 534.21(C₄₀H₂₆N₂ = 534.66) 2-100 m/z = 660.26(C₅₀H₃₂N₂= 660.82) 2-101 m/z = 584.23(C₄₄H₂₈N₂ = 584.72) 2-102 m/z =634.24(C₄₈H₃₀N₂ = 634.78) 2-103 m/z = 584.23(C₄₄H₂₈N₂ = 584.72) 2-104m/z = 660.26(C₅₀H₃₂N₂ = 660.82) 2-105 m/z = 534.21(C₄₀H₂₆N₂ = 534.66)2-106 m/z = 534.21(C₄₀H₂₆N₂ = 534.66) 2-107 m/z = 525.16(C₃₈H₂₃NS =525.67) 2-108 m/z = 551.17(C₄₀H₂₅NS = 551.71) 2-109 m/z =601.19(C₄₄H₂₇NS = 601.77) 2-110 m/z = 525.16(C₃₈H₂₃NS = 525.67) 2-111m/z = 499.14(C₃₆H₂₁NS = 499.63) 2-112 m/z = 499.14(C₃₆H₂₁NS = 499.63)2-113 m/z = 573.22(C₄₂H₂₇N₃ = 573.7) 2-114 m/z = 565.15(C₄₀H₂₃NOS =565.69) 2-115 m/z = 555.11(C₃₈H₂₁NS₂ = 555.71) 2-116 m/z =627.18(C₄₄H₂₅N₃S = 627.77) 2-117 m/z = 487.14(C₃₅H₂₁NS = 487.62) 2-118m/z = 727.23(C₅₄H₃₃NS = 727.93) 2-119 m/z = 535.19(C₄₀H₂₅NO = 535.65)2-120 m/z = 509.18(C₃₈H₂₃NO = 509.61) 2-121 m/z = 535.19(C₄₀H₂₅NO =535.65) 2-122 m/z = 485.21(C₃₇H₂₇N = 485.63) 2-123 m/z = 561.25(C₄₃H₃₁N= 561.73) 2-124 m/z = 603.18(C₄₂H₂₅N₃S = 603.74) 2-125 m/z =683.26(C₅₃H₃₃N = 683.85) 2-126 m/z = 521.21(C₄₀H₂₇N = 521.66) 2-127 m/z= 561.25(C₄₃H₃₁N = 561.73) 2-128 m/z = 739.27(C₅₃H₃₃N₅ = 739.88) 2-129m/z = 548.19(C₄₀H₂₄N₂O = 548.65) 2-130 m/z = 598.2(C₄₄H₂₆N₂O = 598.71)2-131 m/z = 564.17(C₄₀H₂₄N₂S = 564.71) 2-132 m/z = 640.2(C₄₆H₂₈N₂S =640.8) 2-133 m/z = 489.12(C₃₄H₁₉NOS = 489.59) 2-134 m/z =505.1(C₃₄H₁₉NS₂ = 505.65) 2-135 m/z = 598.2(C₄₄H₂₆N₂O = 598.71) 2-136m/z = 564.17(C₄₀H₂₄N₂S = 564.71) 2-137 m/z = 548.19(C₄₀H₂₄N₂O = 548.65)2-138 m/z = 581.13(C₄₀H₂₃NS₂ = 581.75) 2-139 m/z = 539.13(C₃₈H₂₁NOS =539.65) 2-140 m/z = 615.17(C₄₄H₂₅NOS = 615.75) 2-141 m/z =489.12(C₃₄H₁₉NOS = 489.59) 2-142 m/z = 489.12(C₃₄H₁₉NOS = 489.59) 2-143m/z = 589.15(C₄₂H₂₃NOS = 589.71) 2-144 m/z = 605.13(C₄₂H₂₃NS₂ = 605.77)2-145 m/z = 664.2(C₄₈H₂₈N₂S = 664.83) 2-146 m/z = 539.13(C₃₈H₂₁NOS =539.65) 2-147 m/z = 548.19(C₄₀H₂₄N₂O = 548.65) 2-148 m/z =774.27(C₅₈H₃₄N₂O = 774.92) 2-149 m/z = 690.21(C₅₀H₃₀N₂S = 690.86) 2-150m/z = 651.26(C₄₉H₃₃NO = 651.81) 2-151 m/z = 548.19(C₄₀H₂₄N₂O = 548.65)2-152 m/z = 548.19(C₄₀H₂₄N₂O = 548.65) 2-153 m/z = 640.2(C₄₆H₂₈N₂S =640.8) 2-154 m/z = 505.1(C₃₄H₁₉NS₂ = 505.65) 2-155 m/z =549.17(C₄₀H₂₃NO₂ = 549.63) 2-156 m/z = 489.12(C₃₄H₁₉NOS = 489.59) 2-157m/z = 598.2(C₄₄H₂₆N₂O = 598.71) 2-158 m/z = 665.18(C₄₈H₂₇NOS = 665.81)2-159 m/z = 624.22(C₄₆H₂₈N₂O = 624.74) 2-160 m/z = 724.25(C₅₄H₃₂N₂O =724.86) 2-161 m/z = 640.2(C₄₆H₂₈N₂S = 640.8) 2-162 m/z = 598.2(C₄₄H₂₆N₂O= 598.71) 2-163 m/z = 691.2(C₅₀H₂₉NOS = 691.85) 2-164 m/z =589.15(C₄₂H₂₃NOS = 589.71) 2-165 m/z = 548.19(C₄₀H₂₄N₂O = 548.65) 2-166m/z = 640.2(C₄₆H₂₉N₂S = 640.8)

Manufacturing and Evaluation of Organic Electric Element [Example 1] to[Example 15] Red OLED (Phosphorescent Host)

On the ITO layer (anode) formed on the glass substrate,4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter,abbreviated as “2-TNATA”) was vacuum deposited to a thickness of 60 nmto form a hole injection layer. Then,N,N′-bis(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine(hereinafter abbreviated as “NPB”) was vacuum deposited to a thicknessof 55 nm to form a hole transport layer.

Next, a light emitting layer having a thickness of 30 nm was depositedon the hole transport layer by using compound shown in Table 7 belowamong the compounds represented by Formula 2-K of the present inventionas a host material andbis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter,abbreviated as “(piq)₂Ir(acac)”) as a dopant material, wherein theweight ratio of the host and the dopant was 95:5.

Next, (1,1′-bisphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, “BAlq”) was vacuum-deposited to a thickness of 5 nm on thelight emitting layer to form a hole blocking layer, andbis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter, “BeBq₂”) wasvacuum-deposited to a thickness of 45 nm on the hole blocking layer toform a an electron transport layer. Thereafter, LiF was deposited to athickness of 0.2 nm to form an electron injection layer on the electrontransport layer, and then Al was deposited to a thickness of 150 nm toform a cathode on the electron injection layer. In this way, OLED wasmanufactured.

[Comparative Example 1] to [Comparative Example 3]

The organic electroluminescent element was manufactured in the samemanner as described in Example 1 except that one of the followingComparative Compounds 1 to 3, instead of compound of the presentinvention, was used as host material of the light emitting layer.

Electroluminescence characteristics were measured with a PR-650 (Photoresearch) by applying a forward bias DC voltage to the OLEDs prepared inExamples 1 to 15 of the present invention and Comparative Examples 1 to3. T(95) life time was measured using a life time measuring apparatusmanufactured by Mc science Inc. at reference brightness of 2500 cd/in².The measurement results are shown in the table 7 below.

TABLE 7 Current Voltage Density Brightness Efficiency Lifetime CIECompound (V) (mA/cm²) (cd/m²) (cd/A) T (95) X Y comp. Ex (1) Comp. compd1 6.1 17.1  2500 14.6 98.4  0.66 0.33 comp. Ex (2) Comp. compd 2 6.221.7  2500 11.5 102.6  0.66 0.33 comp. Ex (3) Comp. compd 3 5.9 13.9 2500 18.0 107.9  0.66 0.34 Ex. (1)  Com. 2-129 5.4 9.8 2500 25.5 131.8 0.66 0.34 Ex. (2)  Com. 2-130 5.5 9.9 2500 25.3 130.3  0.66 0.34 Ex.(3)  Com. 2-131 5.5 9.7 2500 25.8 129.9  0.67 0.33 Ex. (4)  Com. 2-1375.4 10.4  2500 24.1 125.2  0.67 0.33 Ex. (5)  Com. 2-143 5.6 11.1  250022.5 139.1  0.66 0.33 Ex. (6)  Com. 2-147 5.4 10.2  2500 24.4 127.6 0.66 0.34 Ex. (7)  Com. 2-148 5.5 10.5  2500 23.8 124.4  0.66 0.34 Ex.(8)  Com. 2-149 5.5 10.0  2500 25.0 126.2  0.66 0.33 Ex. (9)  Com. 2-1525.7 10.8  2500 23.2 123.2  0.66 0.34 Ex. (10) Com. 2-153 5.5 10.1  250024.8 130.6  0.66 0.34 Ex. (11) Com. 2-154 5.0 11.4  2500 22.0 140.7 0.66 0.34 Ex. (12) Com. 2-157 5.4 9.8 2500 25.4 131.4  0.67 0.33 Ex.(13) Com. 2-158 5.6 11.6  2500 21.5 135.8  0.67 0.33 Ex. (14) Com. 2-1595.5 10.5  2500 23.7 126.5  0.66 0.33 Ex. (15) Com. 2-160 5.7 10.3  250024.2 125.6  0.66 0.34

From Table 7 above, it can be seen that the electric element using thecompound represented by Formula 2-K of the present invention asphosphorescent host material of the light emitting layer has a lowerdriving voltage and significantly improved efficiency and lifespancompared to the case where Comparative Compound is used.

Comparative Compounds 1 to 3 and the compounds used in Examples of thepresent invention are similar in that they have a heterocyclic group asa basic skeleton as an N-substituent of a polycyclic compound. However,in the compound of the present invention, naphtho[2,3-b]benzofuran isbonded to (substituted for) N of the carbazole moiety of the polycycliccore being 5 or more rings via L (single bond or C₁-C₁₂ arylen group),whereas Comparative Compound 1 is different from the present inventionin that one of the N-substituents of the N—N 5-ring core isdibenzofuran. Comparative Compound 2 differs from the present inventionin that naphtho[2,3-b]benzofuran is bonded to the N-substituent group ofthe N—S 7-ring core via an anthracene(C₁₄) linkage, and ComparativeCompound 3 is different from the present invention in that one of theN-substituents of the N—N 5-ring core is naphtho[1,2-b]benzofuran.

Comparing Comparative Examples 1 and 3, the element characteristics arebetter when the Comparative Compound 3 comprising 2,3-naphthobenzofuranis used as host than when Comparative Compound 1 in which dibenzofuranis introduced as an N-substituent to the N—N 5-ring core is used.

Comparing Comparative Examples 2 and 3, they are identical in that anaphthobenzofuran is introduced as an N-substituent to the core of thepolycyclic ring. However, there is a difference in that ComparativeCompound 2 is an N—S 7-membered ring core, and 2,3-naphthobenzofuran asan N-substituent is introduced via anthracene, whereas Comparativecompound 3 is an N—N 5-membered ring core and 1,2-naphthobenzofuran isdirectly bonded to the core. The driving voltage was lowered and theefficiency was significantly improved, but the lifespan was slightlyreduced in the case of Comparative Example 3 using Comparative Compound3, compared to Comparative Example 2.

In the case of Comparative Compound 2, the physical properties of thecompound change due to the hetero element characteristics included inthe N—S polycyclic compound core, and thus, it seems that the lifespanof the element is slightly improved. However, anthracene being a bulkylinking group is introduced between the core and the N-substituent, andthus, it seems that the driving voltage and efficiency of the elementare lowered.

On the other hand, in the compound represented by Formula 2-K of thepresent invention, 2,3-naphthobenzofuran or 2,3-naphthobenzothiophene isintroduced as an N-substituent of the polycyclic heterocyclic core, andwhen a linking group is introduced between the polycyclic heterocycliccore and 2,3-naphthobenzofuran or 2,3-naphthobenzothiophene, the linkinggroup is restricted to a C₆-C₁₂ arylene group (especially, the compoundused in Examples is C₆). When the compound represented by Formula 2-K ofthe present invention was used as host (Examples 1 to 15), the elementcharacteristics were significantly improved compared to ComparativeExamples 1 to 3.

Referring to Table 8, this will be explained. It can be seen thatComparative Compound 1 has the highest T1 value, Comparative Compound 2has the smallest T1 value, and Comparative Compound 3 has a slightlysmaller T1 value than Comparative Compound 1, and T1 values of compounds2-147, 2-152 and 2-158 of the present invention are located in themiddle range of these comparative compounds (error range of the medianvalue of the minimum and maximum T1 values of the comparative compounds1 to 3±0.3).

TABLE 8 Comp. Comp. Comp. compd 1 compd 2 compd 3 2-147 2-152 2-158 T12.76 1.76 2.67 2.41 2.38 2.39

The difference in the T1 values in Table 8 suggests that the physicalproperties of the compound may be remarkably changed depending on thedegree of molecular bending and the type of the linking group. It seemsthat the element characteristics are improved when the compoundrepresented by Formula 2-K of the present invention is used since thecompound has an appropriate T1 value for easy red emission compared tothe compounds used in Comparative Examples 1 to 3.

The element results of the compound of the present invention and thecomparative compounds suggests that the energy level (HOMO, LUMO, T1,etc.) of the compound may vary significantly depending on the type ofsubstituent constituting the compound, the substitution position, andthe type of heteroatom and a difference in properties of compound mayact as a major factor in improving element performance during theelement deposition, resulting in different element results. Furthermore,it can be confirmed that when 2,3-fused DBF/DBT having a linearstructure in the direction of condensation of fused DBT/DBF amongN-containing polycyclic compounds is introduced as an N-substituent likethe compound represented by Formula 2-K of the present invention, thisis a structure suitable for improving performance of the element.

[Example 16] Mixed Phosphorescent Host of a Light Emitting Layer

On the ITO layer (anode) formed on the glass substrate, 2-TNATA wasvacuum deposited to a thickness of 60 nm to form a hole injection layer.Then, NPB was vacuum deposited to a thickness of 55 nm to form a holetransport layer.

Next, a light emitting layer with a thickness of 30 nm was formed on thehole transport layer, wherein a mixture of a compound 1-61 of thepresent invention (host 1) and a compound 2-36 of the present invention(host 2) in a weight ratio of 3:7 was used as a host and (piq)₂Ir(acac)was used as a dopant and the host and dopant were used in a weight ratioof 95:5.

Next, a film of a mixture of (8-hydroxyquinoline)aluminum (hereinafterabbreviated as “Alq”) and BeBq₂ in a weight ratio of 1:1 was depositedon the hole blocking layer to form an electron transport layer having athickness of 45 nm. Next, LiF on the electron transport layer wasdeposited to a thickness of 0.2 nm and then Al was deposited to athickness of 150 nm to form a cathode. In this way, the OLED wasmanufactured.

[Example 17] to [Example 120]

The organic electroluminescent elements were manufactured in the samemanner as described in Example 16, except that a mixture of the firsthost compound (host 1) and the second host compound (host 2) describedin the following Table 9 was used as host material of the light emittinglayer.

[Comparative Example 4] to [Comparative Example 7]

The OLEDs were manufactured in the same manner as described in Example16, except that a single compound 1-92, compound 1-160, compound 2-129or compound 2-143 as listed in the following Table 9 was used as host ofthe light emitting layer, respectively.

[Comparative Example 8] to [Comparative Example 10]

The OLEDs were manufactured in the same manner as described in Example16 except that a mixture of Comparative compounds 4 and 6 or a mixtureof Comparative compounds 4 and 7 as listed in the following Table 9 wasused as host of a light emitting layer, respectively.

Electroluminescence characteristics were measured with a PR-650 (Photoresearch) by applying a forward bias DC voltage to the OLEDs prepared inExamples 16 to 120 of the present invention and Comparative Examples 4to 10. T(95) life time was measured using a life time measuringapparatus manufactured by Mc science Inc. at reference brightness of2500 cd/m². The measurement results are shown in the table 9 below.

TABLE 9 Current Voltage Density Brightness Efficiency Lifetime Host 1Host 2 (V) (mA/cm²) (cd/m²) (cd/A) T (95) comp. Ex (4)  Com. 1-92  5.813.4  2500 18.6 122   comp. Ex (5)  Com. 1-160 5.9 14.5  2500 17.3 110.7comp. Ex (6)  Com. 2-129 5.8 13.2  2500 18.9 115.2 comp. Ex (7)  Com.2-143 5.9 14.2  2500 17.6 117.8 comp. Ex (8)  Comp. compd 4 Comp. compd5 5.7 12.4  2500 20.1 124.1 comp. Ex (9)  Comp. compd 4 Comp. compd 65.6 12.2  2500 20.5 125.7 comp. Ex (10) Comp. compd 4 Comp. compd 7 5.511.7  2500 21.3 130.4 Ex. (16)  Com. 1-61  Com. 2-36  5.0 7.8 2500 32.0145.0 Ex. (17)  Com. 1-91  4.9 7.5 2500 33.5 145.5 Ex. (18)  Com. 1-92 4.9 7.4 2500 33.7 145.7 Ex. (19)  Com. 1-103 4.9 7.5 2500 33.4 145.3 Ex.(20)  Com. 1-121 5.0 7.7 2500 32.6 146.3 Ex. (21)  Com. 1-122 5.0 7.72500 32.3 145.8 Ex. (22)  Com. 1-145 5.0 7.8 2500 32.2 145.1 Ex. (23) Com. 1-148 5.0 7.4 2500 33.8 145.4 Ex. (24)  Com. 1-149 5.0 7.4 250034.0 145.5 Ex. (25)  Com. 1-151 5.0 7.5 2500 33.2 145.3 Ex. (26)  Com.1-158 5.0 7.6 2500 32.8 146.2 Ex. (27)  Com. 1-160 4.9 7.6 2500 32.9146.5 Ex. (28)  Com. 1-172 5.0 7.7 2500 32.5 146.0 Ex. (29)  Com. 1-1734.9 7.6 2500 32.9 146.8 Ex. (30)  Com. 1-174 4.9 7.6 2500 33.1 147.0 Ex.(31)  Com. 1-61  Com. 2-64  4.8 6.6 2500 37.6 148.8 Ex. (32)  Com. 1-91 4.9 6.4 2500 39.3 149.5 Ex. (33)  Com. 1-92  4.8 6.3 2500 39.4 149.7 Ex.(34)  Com. 1-103 4.9 6.4 2500 39.1 149.1 Ex. (35)  Com. 1-121 4.8 6.62500 38.1 150.3 Ex. (36)  Com. 1-122 4.8 6.6 2500 37.9 149.8 Ex. (37) Com. 1-145 4.8 6.6 2500 37.8 148.9 Ex. (38)  Com. 1-148 4.9 6.3 250039.4 149.2 Ex. (39)  Com. 1-149 4.9 6.3 2500 39.6 149.4 Ex. (40)  Com.1-151 4.9 6.4 2500 39.0 149.1 Ex. (41)  Com. 1-158 Com. 2-64  4.8 6.52500 38.2 150.1 Ex. (42)  Com. 1-160 4.8 6.5 2500 38.5 150.4 Ex. (43) Com. 1-172 4.9 6.6 2500 38.0 150.0 Ex. (44)  Com. 1-173 4.9 6.5 250038.7 150.5 Ex. (45)  Com. 1-174 4.9 6.4 2500 38.9 150.7 Ex. (46)  Com.1-61  Com. 2-105 4.9 7.0 2500 35.8 147.1 Ex. (47)  Com. 1-91  4.9 6.72500 37.2 147.9 Ex. (48)  Com. 1-92  4.8 6.7 2500 37.4 148.0 Ex. (49) Com. 1-103 4.9 6.7 2500 37.1 147.5 Ex. (50)  Com. 1-121 4.8 6.9 250036.0 148.6 Ex. (51)  Com. 1-122 4.8 7.0 2500 35.9 148.0 Ex. (52)  Com.1-145 4.9 7.0 2500 35.9 147.2 Ex. (53)  Com. 1-148 4.8 6.6 2500 37.6147.5 Ex. (54)  Com. 1-149 4.8 6.6 2500 37.8 147.7 Ex. (55)  Com. 1-1514.8 6.8 2500 36.8 147.4 Ex. (56)  Com. 1-158 4.8 6.9 2500 36.2 148.3 Ex.(57)  Com. 1-160 4.9 6.9 2500 36.2 148.6 Ex. (58)  Com. 1-172 4.8 6.92500 36.0 148.2 Ex. (59)  Com. 1-173 4.9 6.9 2500 36.4 148.9 Ex. (60) Com. 1-174 4.9 6.8 2500 36.5 149.0 Ex. (61)  Com. 1-61  Com. 2-111 5.07.4 2500 34.0 150.5 Ex. (62)  Com. 1-91  4.9 7.1 2500 35.4 151.4 Ex.(63)  Com. 1-92  4.9 7.0 2500 35.6 151.6 Ex. (64)  Com. 1-103 4.9 7.12500 35.4 151.0 Ex. (65)  Com. 1-121 4.9 7.3 2500 34.3 152.0 Ex. (66) Com. 1-122 5.0 7.3 2500 34.1 151.7 Ex. (67)  Com. 1-145 5.0 7.4 250034.0 150.6 Ex. (68)  Com. 1-148 4.8 7.0 2500 35.8 151.1 Ex. (69)  Com.1-149 4.8 6.9 2500 36.0 151.3 Ex. (70)  Com. 1-151 5.0 7.1 2500 35.1150.9 Ex. (71)  Com. 1-158 4.9 7.3 2500 34.3 152.0 Ex. (72)  Com. 1-1604.9 7.2 2500 34.5 152.1 Ex. (73)  Com. 1-172 4.9 7.3 2600 34.1 151.9 Ex.(74)  Com. 1-173 4.8 7.2 2500 34.7 152.3 Ex. (76)  Com. 1-174 4.8 7.22600 34.8 162.4 Ex. (76)  Com. 1-61  Com. 2-113 5.1 8.3 2600 30.0 141.5Ex. (77)  Com. 1-91  5.0 7.9 2500 31.5 142.8 Ex. (78)  Com. 1-92  5.07.9 2600 31.7 143.0 Ex. (79)  Com. 1-103 5.1 8.0 2600 31.3 142.2 Ex.(80)  Com. 1-121 5.1 8.1 2500 30.7 144.1 Ex. (81)  Com. 1-122 5.1 8.22500 30.4 143.2 Ex. (82)  Com. 1-145 5.1 8.3 2600 30.3 141.8 Ex. (83) Com. 1-148 5.1 7.8 2500 31.9 142.4 Ex. (84)  Com. 1-149 5.1 7.8 250032.0 142.7 Ex. (85)  Com. 1-151 5.0 8.0 2600 31.3 142.0 Ex. (86)  Com.1-168 5.0 8.1 2600 30.7 143.9 Ex. (87)  Com. 1-160 5.0 8.1 2500 30.8144.4 Ex. (88)  Com. 1-172 5.1 8.2 2600 30.6 143.5 Ex. (89)  Com. 1-1735.0 8.0 2600 31.1 144.6 Ex. (90)  Com. 1-174 5.0 8.0 2500 31.2 144.9 Ex.(91)  Com. 1-61  Com. 2-129 4.8 6.1 2600 41.2 152.2 Ex. (92)  Com. 1-91 4.7 5.9 2600 42.6 152.9 Ex. (93)  Com. 1-92  4.7 5.8 2500 42.8 153.0 Ex.(94)  Com. 1-103 4.8 5.9 2500 42.5 152.5 Ex. (95)  Com. 1-121 4.8 6.02600 41.7 153.5 Ex. (96)  Com. 1-122 4.8 6.0 2500 41.4 153.1 Ex. (97) Com. 1-145 4.7 6.1 2500 41.3 152.3 Ex. (98)  Com. 1-148 4.8 6.8 260042.9 152.5 Ex. (99)  Com. 1-149 4.8 5.8 2500 43.1 152.7 Ex. (100) Com.1-151 4.8 5.9 2500 42.4 152.5 Ex. (101) Com. 1-158 4.8 6.0 2600 41.8153.3 Ex. (102) Com. 1-160 4.7 6.0 2600 41.9 153.7 Ex. (103) Com. 1-1724.8 6.0 2500 41.5 153.3 Ex. (104) Com. 1-173 4.7 6.0 2500 42.0 153.8 Ex.(105) Com. 1-174 4.7 5.9 2500 42.2 154.1 Ex. (106) Com. 1-61  Com. 2-1434.8 6.3 2500 39.4 153.9 Ex. (107) Com. 1-91  4.7 6.1 2500 40.9 154.8 Ex.(108) Com. 1-92  4.7 6.1 2500 41.1 154.9 Ex. (109) Com. 1-103 4.7 6.12500 40.7 154.2 Ex. (110) Com. 1-121 4.8 6.3 2500 40.0 155.3 Ex. (111)Com. 1-122 4.8 6.3 2500 39.7 155.0 Ex. (112) Com. 1-145 4.7 6.3 250039.6 154.0 Ex. (113) Com. 1-148 4.8 6.1 2500 41.3 154.3 Ex. (114) Com.1-149 4.8 6.0 2500 41.4 154.5 Ex. (115) Com. 1-151 4.8 6.1 2500 40.7154.1 Ex. (116) Com. 1-158 4.8 6.2 2500 40.2 155.2 Ex. (117) Com. 1-1604.7 6.2 2500 40.3 155.3 Ex. (118) Com. 1-172 4.8 6.3 2500 39.9 155.0 Ex.(119) Com. 1-173 4.7 6.2 2500 40.5 155.6 Ex. (120) Com. 1-174 4.7 6.22500 40.6 155.8

From Table 9, it can be seen that the driving voltage, efficiency andlifetime were remarkably improved when the mixture of the compounds foran organic electroluminescent element of the present inventionrepresented by Formula 1 and Formula 2 was used as a phosphorescent host(Examples 16 to 120), compared to element using a single material(Comparative Examples 4 to 7), the mixture of Comparative Compounds 4 to7 (Comparative Examples 8 to 10).

Comparing Comparative Examples 4 to 10, Comparative Examples 8 to 10, inwhich two compounds were mixed and used as a host, exhibited improvedelement characteristics compared to Comparative Examples 4 and 5 usingthe compound of the present invention represented by Formula 1 as asingle host, or compared to Comparative Examples 6 and 7 in which thecompound of the present invention represented by Formula 2 was used as asingle host.

In addition, the driving voltage of the element is lowered, and theefficiency and lifespan is significantly improved when the mixture ofcompounds represented by Formula 1 and Formula 2 of the presentinvention are used (Example 16 to Example 120) than when the mixture ofthe comparative compounds are used (Comparative Examples 8 to 10).

From these results, the inventors of the present invention believed thata mixture of compounds of Formulas 1 and 2 has novel characteristicsother than those of each compound, and thus the PL lifetime for each ofthese compounds and mixtures were measured. As a result, it wasconfirmed that a new PL wavelength for the mixture of compounds ofFormula 1 and 2 of the present invention was formed unlike a singlecompound.

It seems that this is because when a mixture of compounds of the presentinvention is used, electrons and holes move or energy is transferredthrough a new region (exciplex) having a new energy level formed bymixing as well as the energy level of each substance, as a result,efficiency and lifetime are increased. This is an important example inwhich the mixed thin film shows exciplex energy transfer and lightemission processes when the mixture of the present invention is used.

In addition, when a mixture of a polycyclic compound of Formula 1 whichhas a high T1 value with high stability to not only electrons but alsoholes and compound of Formula 2 which has strong hole properties wasused, the charge balance of hoe and electron in the light emitting layerincreases, and thus light emission occurs well inside the light-emittinglayer, not the interface of the hole transport layer. As a result, thedeterioration in the interface of a hole transport layer is alsoreduced, thereby maximizing the driving voltage, efficiency and lifetimeof the element. Therefore, it seems that the overall performance of theelement was improved due to electrochemical synergy when the mixture ofcompounds of Formulas 1 and 2 was used.

[Example 121] to [Example 126]

An OLED was manufactured in the same manner as in Example 16, exceptthat the first host and the second host were mixed in a certain ratio asshown in Table 10 below.

Electroluminescence characteristics were measured with a PR-650 (Photoresearch) by applying a forward bias DC voltage to the OLEDs prepared inExamples 121 to 126 of the present invention. T(95) life time wasmeasured using a life time measuring apparatus manufactured by Mcscience Inc. at reference brightness of 2500 cd/m². The measurementresults are shown in the table 10 below. Examples 33 and 93 show theresults of measuring the elements characteristics when host 1 and host 2were mixed in a ratio of 3:7 and used as a host as in Table 9.

TABLE 10 Current Mixing ratio Voltage Density Brightness EfficiencyLifetime Host 1 Host 2 (Host 1:Host 2) (V) (mA/cm²) (cd/m²) (cd/A) T(95) Ex. (121) 1-92  2-64  7:3 4.9 6.5 2500 38.2 148.2 Ex. (122) 5:5 4.96.4 2600 39.1 149.0 Ex. (33)  3:7 4.8 6.3 2500 39.4 149.7 Ex. (123)1-121 2-111 7:3 5.1 7.6 2500 33.0 150.1 Ex. (124) 5:5 5.0 7.4 2600 33.9151.4 Ex. (65)  3:7 4.9 7.3 2500 34.3 152.0 Ex. (125) 1-92  2-129 7:34.9 6.0 2500 41.8 152.1 Ex. (126) 5:5 4.8 5.9 2500 42.5 152.7 Ex. (93) 3:7 4.7 5.8 2500 42.6 153.0

Referring to Table 10, it can be seen that the driving voltage,efficiency and lifespan are the best when the mixing ratio of the firsthost and the second host was 3:7, and the element characteristics aredeteriorated as the amount of the first host was increased. This isbecause the charge balance in the light emitting layer is maximized asthe amount of the compound represented by Formula 2, which hasrelatively stronger hole characteristics than that of Formula 1, isincreased.

Although the exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art to whichthe present invention pertains will be capable of various modificationswithout departing from the essential characteristics of the presentinvention. Therefore, the embodiments disclosed in this specificationare not intended to limit the present invention, but to illustrate thepresent invention, and the spirit and scope of the present invention arenot limited by the embodiments. The scope of the present invention shallbe construed on the basis of the accompanying claims, and it shall beconstrued that all of the technical ideas included within the scopeequivalent to the claims belong to the present invention.

What is claimed is:
 1. A compound of Formula 2-K:

wherein: W¹ and W² are each independently a single bond, N-L′-(Ar⁴), O,S or C(R^(′))(R^(″)), with the proviso that both W¹ and W² are not asingle bond at the same time, W³ is O or S, L⁴ is a single bond or aC₆-C₁₂ arylene group, R² to R⁴, R¹¹ and R^(′) and R^(″) are eachindependently selected from the group consisting of hydrogen, deuterium,halogen, a cyano group, a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀heterocyclic group comprising at least one heteroatom selected from thegroup consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fusedring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀alkoxyl group, a C₆-C₃₀ aryloxy group and -L′-N(R_(a))(R_(b)), andadjacent R²s, adjacent R³s, adjacent R⁴s or adjacent R¹¹s may be bondedto each other to form a ring, and R^(′) and R^(″) may be bonded to eachother to form a ring, b and d are each an integer of 0 to 4, c is aninteger of 0 to 2, d1 is an integer of 0 to 9, and where each of b, c, dand d1 is an integer of 2 or more, each of a plurality of R²s, each of aplurality of R³s, each of a plurality of R⁴s and each of a plurality ofR¹¹s are the same as or different from each other, Ar⁴ is selected fromthe group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀heterocyclic group comprising at least one heteroatom selected from thegroup consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fusedring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀alkoxyl group and a C₆-C₃₀ aryloxy group, L′ is selected from the groupconsisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylenegroup, a C₂-C₆₀ heterocyclic group comprising at least one heteroatomselected from the group consisting of O, N, S, Si and P, a C₃-C₆₀aliphatic ring, and a fused ring of a C₃-C₆₀ aliphatic ring with aC₆-C₆₀ aromatic ring, R_(a) and R_(b) are each independently selectedfrom the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, aC₂-C₆₀ heterocyclic group comprising at least one heteroatom selectedfrom the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring,and a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring,and R² to R⁴, Ar⁴, L⁴, L′, R_(a), R_(b), R^(′), R^(″), the ring formedby adjacent groups, and the ring formed by R^(′) and R^(″) may be eachoptionally substituted with one or more substituents selected from thegroup consisting of deuterium, halogen, a silane group unsubstituted orsubstituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxanegroup, a boron group, a germanium group, a cyano group, a nitro group, aC₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, aC₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, afluorenyl group, a C₂-C₂₀ heterocyclic group containing at least oneheteroatom of O, N, S, Si, and P, a C₃-C₂₀ aliphatic ring group, aC₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group.
 2. The compound ofclaim 1, wherein Formula 2-K is represented by Formula 2-K-1:

wherein W¹ to W³, R² to R⁴, R¹¹, L⁴, b to d and d1 are the same asdefined in claim
 1. 3. The compound of claim 1, wherein Formula 2-K isrepresented by Formula 2-K-2:

wherein W¹, W³, R² to R⁴, R¹¹, L⁴, b to d and d1 are the same as definedin claim
 1. 4. The compound of claim 1, wherein W¹ is N-L′-(Ar⁴).
 5. Thecompound of claim 1, wherein W¹ is N-L′-(Ar⁴) and W² is a single bond.6. The compound of claim 1, wherein at least one of L′ and Ar⁴ issubstituted with one or more substituents selected from the groupconsisting of deuterium, halogen, a C₆-C₂₀ aryl group, a C₆-C₂₀ arylgroup substituted with deuterium, a fluorenyl group, a C₂-C₂₀heterocyclic group containing at least one heteroatom of O, N, S, Si,and P, and a C₃-C₂₀ aliphatic ring group.
 7. The compound of claim 1,wherein at least one of L′ and Ar⁴ is substituted with deuterium.
 8. Thecompound of claim 1, wherein Ar⁴ is a C₆-C₆₀ aryl group, a fluorenylgroup, or a C₂-C₆₀ heterocyclic group comprising at least one heteroatomselected from the group consisting of O, N, S, Si and P.
 9. The compoundof claim 8, wherein Ar⁴ is substituted with deuterium or a C₆-C₂₀ arylgroup substituted with deuterium.
 10. The compound of claim 1, whereinthe compound of Formula 2-K is one of the following compounds:


11. An organic electric element comprising a first electrode, a secondelectrode, and an organic material layer formed between the firstelectrode and the second electrode, wherein the organic material layercomprises a compound of Formula 2-K of claim
 1. 12. The organic electricelement of claim 11, wherein the organic material layer comprises alight emitting layer, and the light emitting layer comprises thecompound of Formula 2-K.
 13. An electronic device comprising a displaydevice and a control unit for driving the display device, wherein thedisplay device comprises the organic electric element of claim
 11. 14.The electronic device of claim 13, wherein the organic electric elementis selected from the group consisting of an organic light emittingdiode, an organic solar cell, an organic photo conductor, an organictransistor, an element for monochromatic illumination and a quantum dotdisplay.